{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,4,3]],"date-time":"2026-04-03T03:50:28Z","timestamp":1775188228466,"version":"3.50.1"},"reference-count":134,"publisher":"MDPI AG","issue":"1","license":[{"start":{"date-parts":[[2025,12,19]],"date-time":"2025-12-19T00:00:00Z","timestamp":1766102400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Nitrones are a significant class of compounds highly useful in organic synthesis; in particular, they are key intermediates for the synthesis of new biologically active nitrogen compounds. The first part of this review aims to provide a structured and concise overview of nitrones, summarizing their synthetic methodologies and highlighting the environmentally friendly approaches. Their fundamental transformations and a thorough explanation of their reactivities are addressed, either in rearrangements to similar compounds or as fragments\/intermediates for more complex molecules. Lastly, physicochemical properties, therapeutic potential, and industrial applications are also addressed. This review gives an update on the scientific discoveries in the field of nitrones, focusing on organizing the existing information and highlighting subtle details to enhance chemical comprehension.<\/jats:p>","DOI":"10.3390\/molecules31010013","type":"journal-article","created":{"date-parts":[[2025,12,22]],"date-time":"2025-12-22T07:01:33Z","timestamp":1766386893000},"page":"13","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":1,"title":["Nitrones: Comprehensive Review on Synthesis and Applications"],"prefix":"10.3390","volume":"31","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-1633-7153","authenticated-orcid":false,"given":"Ricardo A. L. S.","family":"Santos","sequence":"first","affiliation":[{"name":"LAQV-REQUIMTE, Department of Chemistry, University of Aveiro, 3010-193 Aveiro, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2861-8286","authenticated-orcid":false,"given":"Artur M. S.","family":"Silva","sequence":"additional","affiliation":[{"name":"LAQV-REQUIMTE, Department of Chemistry, University of Aveiro, 3010-193 Aveiro, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4249-7089","authenticated-orcid":false,"given":"Diana C. G. A.","family":"Pinto","sequence":"additional","affiliation":[{"name":"LAQV-REQUIMTE, Department of Chemistry, University of Aveiro, 3010-193 Aveiro, Portugal"}]}],"member":"1968","published-online":{"date-parts":[[2025,12,19]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"3331","DOI":"10.1002\/cber.189002302295","article-title":"Zur kenntniss der aldoxime. VII, Ber","volume":"23","author":"Beckmann","year":"1890","journal-title":"Dtsch. Chem. Ges."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"193","DOI":"10.1021\/cr60075a001","article-title":"Aliphatic diazo compounds, nitrones, and structurally analogous compounds. systems capable of undergoing 1,3-additions","volume":"23","author":"Smith","year":"1938","journal-title":"Chem. Rev."},{"key":"ref_3","doi-asserted-by":"crossref","unstructured":"Feuer, H. (2008). Nitrile Oxides, Nitrones and Nitronates in Organic Synthesis: Novel Strategies in Synthesis, John Wiley & Sons. [2nd ed.].","DOI":"10.1002\/9780470191552"},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"473","DOI":"10.1021\/cr60230a006","article-title":"Nitrones","volume":"64","author":"Hamer","year":"1964","journal-title":"Chem. Rev."},{"key":"ref_5","doi-asserted-by":"crossref","unstructured":"Favre, H.A., and Powell, W.H. (2013). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013, Royal Society of Chemistry.","DOI":"10.1039\/9781849733069"},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"5366","DOI":"10.1021\/cr5007182","article-title":"Recent advances of catalytic asymmetric 1,3-dipolar cycloadditions","volume":"115","author":"Hashimoto","year":"2015","journal-title":"Chem. Rev."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"9","DOI":"10.1002\/ajoc.201500211","article-title":"Diverse applications of nitrones for the synthesis of heterocyclic compounds","volume":"5","author":"Anderson","year":"2016","journal-title":"Asian J. Org. Chem."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"116","DOI":"10.1039\/C5QO00122F","article-title":"New developments of ketonitrones in organic synthesis","volume":"3","author":"Shi","year":"2016","journal-title":"Org. Chem. Front."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"4684","DOI":"10.1021\/acs.chemrev.8b00476","article-title":"Synthesis and transformations of nitrones for organic synthesis","volume":"119","author":"Murahashi","year":"2019","journal-title":"Chem. Rev."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"731","DOI":"10.1248\/cpb.c24-00343","article-title":"Exploration and development of nitrone chemistry","volume":"72","author":"Tamura","year":"2024","journal-title":"Chem. Pharm. Bull."},{"key":"ref_11","doi-asserted-by":"crossref","unstructured":"Bonnett, R., Brown, R.F.C., Clark, V.M., Sutherland, I.O., and Todd, A. (1959). 423. Experiments towards the synthesis of corrins. Part II. The preparation and reactions of \u03941-pyrroline 1 oxides. J. Chem. Soc., 2094\u20132102.","DOI":"10.1039\/JR9590002094"},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"1068","DOI":"10.1021\/jo01039a048","article-title":"Oxidation of N,N-dialkyl hydroxylamines with t-butyl hydroperoxide. A new synthesis for nitrones","volume":"28","author":"Coppinger","year":"1963","journal-title":"J. Org. Chem."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"7243","DOI":"10.1021\/jo990417r","article-title":"Inexpensive and environmentally friendly oxidation of hydroxylamines to nitrones with bleach","volume":"64","author":"Cicchi","year":"1999","journal-title":"J. Org. Chem."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"1049","DOI":"10.1016\/S0040-4039(00)81600-7","article-title":"The reaction of N-mono an N,N-disubstituted hydroxylamines with palladium catalyst","volume":"24","author":"Murahashi","year":"1983","journal-title":"Tetrahedron Lett."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"14917","DOI":"10.1016\/0040-4020(96)00904-0","article-title":"Regiochemistry of mercury(II) oxide oxidation of unsymmetrical N,N-disubstituted hydroxylamines","volume":"52","author":"Ali","year":"1996","journal-title":"Tetrahedron"},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"6571","DOI":"10.1016\/S0040-4039(00)78275-X","article-title":"Highly efficient and mild synthesis of nitrones by catalytic oxidation of hydroxylamines with tetra-n-propylammonium perruthenate","volume":"35","author":"Goti","year":"1994","journal-title":"Tetrahedron Lett."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"1989","DOI":"10.1016\/S0040-4039(99)00098-2","article-title":"Oxidation of hydroxylamines to nitrones catalyzed by (Salen)Mn(III) complexes. Enantioselective synthesis of a protected cis-dihydroxypyrroline N-oxide with Jacobsen catalyst","volume":"40","author":"Cicchi","year":"1999","journal-title":"Tetrahedron Lett."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"6503","DOI":"10.1016\/S0040-4039(01)01222-9","article-title":"Manganese dioxide oxidation of hydroxylamines to nitrones","volume":"42","author":"Cicchi","year":"2001","journal-title":"Tetrahedron Lett."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"639","DOI":"10.1002\/adsc.200303223","article-title":"Oxidation of N,N-disubstituted hydroxylamines to nitrones with hydrogen peroxide catalyzed by polymer-supported methylrhenium trioxide systems","volume":"346","author":"Saladino","year":"2004","journal-title":"Adv. Synth. Catal."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"6555","DOI":"10.1021\/ja00753a038","article-title":"Kinetic applications of electron paramagnetic resonance spectroscopy. III. Self-reactions of dialkyl nitroxide radicals","volume":"93","author":"Bowman","year":"1971","journal-title":"J. Am. Chem. Soc."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"3219","DOI":"10.1016\/S0040-4039(00)79856-X","article-title":"Peracid induced ring opening of isoxazolidines. A mechanistic study","volume":"33","author":"Ali","year":"1992","journal-title":"Tetrahedron Lett."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"1173","DOI":"10.1021\/ic701402h","article-title":"The mechanism of carbon dioxide catalysis in the hydrogen peroxide N-oxidation of amines","volume":"47","author":"Balagam","year":"2008","journal-title":"Inorg. Chem."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"3561","DOI":"10.1016\/0040-4039(95)00558-T","article-title":"Oxidation of secondary amines to nitrones using urea-hydrogen peroxide complex (UHP) and metal catalysts","volume":"36","author":"Marcantoni","year":"1995","journal-title":"Tetrahedron Lett."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"3547","DOI":"10.1016\/S0040-4039(98)00545-0","article-title":"Oxygenation of aldimines and deoxygenation of nitrones on irradiated TiO2","volume":"39","author":"Somasundaram","year":"1998","journal-title":"Tetrahedron Lett."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"6365","DOI":"10.1021\/jo901108u","article-title":"A metal-free general procedure for oxidation of secondary amines to nitrones","volume":"74","author":"Gella","year":"2009","journal-title":"J. Org. Chem."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"4431","DOI":"10.1021\/ja00351a049","article-title":"Chemical properties of phenanthrolinequinones and the mechanism of amine oxidation by o-quinones of medium redox potentials","volume":"105","author":"Eckert","year":"1983","journal-title":"J. Am. Chem. Soc."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"442","DOI":"10.1021\/jp310501h","article-title":"Reaction mechanism of selective photooxidation of amines over niobium oxide: Visible-light-induced electron transfer between adsorbed amine and Nb2O5","volume":"117","author":"Furukawa","year":"2013","journal-title":"J. Phys. Chem. C"},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"1474","DOI":"10.1021\/jo01280a037","article-title":"Electrochemical oxidation of primary aliphatic amines","volume":"32","author":"Barnes","year":"1967","journal-title":"J. Org. Chem."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"7451","DOI":"10.1021\/jo990769y","article-title":"Practical synthesis of hydroxamate-derived siderophore components by an indirect oxidation method and syntheses of a DIG\u2212siderophore conjugate and a biotin\u2212siderophore conjugate","volume":"64","author":"Lin","year":"1999","journal-title":"J. Org. Chem."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"4692","DOI":"10.1021\/ja00795a037","article-title":"Peracid oxidation of imines. Kinetics and mechanism of competitive formation of nitrones and oxaziranes from cyclic and acyclic imines","volume":"95","author":"Ogata","year":"1973","journal-title":"J. Am. Chem. Soc."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"9460","DOI":"10.1002\/ange.201402878","article-title":"Selective reductive coupling of nitro compounds with aldehydes to nitrones in H2 using carbon-supported and -decorated platinum nanoparticles","volume":"126","author":"Cisneros","year":"2014","journal-title":"Angew. Chem."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"5569","DOI":"10.1016\/j.tet.2008.03.091","article-title":"Solvent-free synthesis of nitrones in a ball-mill","volume":"64","author":"Colacino","year":"2008","journal-title":"Tetrahedron"},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"678","DOI":"10.1055\/s-0029-1218581","article-title":"Synthesis of N-(benzyloxyethyl)- and N-(alkoxycarbonylmethyl)nitrones","volume":"2010","author":"Gultekin","year":"2010","journal-title":"Synthesis"},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"1061","DOI":"10.1016\/S0957-4166(97)00066-9","article-title":"Direct conversion of chiral cyanohydrins to chiral nitrones by transamination","volume":"8","author":"Hulsbos","year":"1997","journal-title":"Tetrahedron Asymmetry"},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"432","DOI":"10.1002\/jhet.84","article-title":"The alkylation of isatin-derived oximes: Spectroscopic and X-ray crystallographic structural characterization of oxime and nitrone products","volume":"46","author":"Sin","year":"2009","journal-title":"J. Heterocycl. Chem."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"22161","DOI":"10.1039\/C6RA02638A","article-title":"Revisiting oxime\u2013nitrone tautomerism. Evidence of nitrone tautomer participation in oxime nucleophilic addition reactions","volume":"6","author":"Tejero","year":"2016","journal-title":"RSC Adv."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"593","DOI":"10.1039\/b210035e","article-title":"Preparation and use as spin trapping agents of new ester -nitrones","volume":"1","author":"Allouch","year":"2003","journal-title":"Org. Biomol. Chem."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"1614","DOI":"10.1021\/jo0523518","article-title":"One-pot synthesis of cyclic nitrones and their conversion to pyrrolizidines:\u2009 7a-epi-crotanecine inhibits \u03b1-mannosidases","volume":"71","author":"Cicchi","year":"2006","journal-title":"J. Org. Chem."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"2097","DOI":"10.3762\/bjoc.11.226","article-title":"Copper-mediated synthesis of N-alkenyl-\u03b1,\u03b2-unsaturated nitrones and their conversion to tri- and tetrasubstituted pyridines","volume":"11","author":"Kontokosta","year":"2015","journal-title":"Beilstein J. Org. Chem."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"7884","DOI":"10.1021\/ja102436z","article-title":"Copper-catalyzed tandem [2,3]-rearrangement and 6\u03c0-3-azatriene electrocyclization in (E)-O-propargylic \u03b1,\u03b2-unsaturated oximes","volume":"132","author":"Nakamura","year":"2010","journal-title":"J. Am. Chem. Soc."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"1388","DOI":"10.1039\/c39920001388","article-title":"Mercuric acetate induced formation of cyclic nitrones from alkenyl oximes","volume":"19","author":"Grigg","year":"1992","journal-title":"J. Chem. Soc., Chem. Commun."},{"key":"ref_42","doi-asserted-by":"crossref","unstructured":"Noguchi, M., Okada, H., Nishimura, S., Yamagata, Y., Takamura, S., Tanaka, M., Kakehi, A., and Yamamoto, H. (1999). A simple oxime\u2013nitrone isomerisation and intramolecular nitrone-cycloaddition reaction of 3-(alk-2-enylamino)propionaldehyde oximes. J. Chem. Soc. Perkin Trans. 1, 185\u2013192.","DOI":"10.1039\/a807542e"},{"key":"ref_43","doi-asserted-by":"crossref","unstructured":"Grigg, R., Hadjisoteriou, M., Kennewell, P., Markandu, J., and Thornton-Pett, M. (1993). Halogen-induced formation of nitrones from oximes and alkenes. J. Chem. Soc., Chem. Commun., 1340\u20131342.","DOI":"10.1039\/c39930001340"},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"1990","DOI":"10.1002\/ange.201308617","article-title":"Inorganic-base-mediated hydroamination of alkenyl oximes for the synthesis of cyclic nitrones","volume":"126","author":"Peng","year":"2014","journal-title":"Angew. Chem."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"6719","DOI":"10.1016\/S0040-4039(01)01346-6","article-title":"A new synthetic access to N-alkylated nitrones through Lewis acid-catalyzed conjugate additions of aldoximes","volume":"42","author":"Nakama","year":"2001","journal-title":"Tetrahedron Lett."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"11702","DOI":"10.1021\/jacs.7b06523","article-title":"Asymmetric nitrone synthesis via ligand-enabled copper-catalyzed Cope-type hydroamination of cyclopropene with oxime","volume":"139","author":"Li","year":"2017","journal-title":"J. Am. Chem. Soc."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"8816","DOI":"10.1002\/anie.201203799","article-title":"Oxime radical promoted dioxygenation, oxyamination, and diamination of alkenes: Synthesis of isoxazolines and cyclic nitrones","volume":"51","author":"Han","year":"2012","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_48","doi-asserted-by":"crossref","unstructured":"Fox, M.E., Holmes, A.B., Forbes, I.T., and Thompson, M. (1994). N-alkenyl nitrone dipolar cycloaddition routes to piperidines and indolizidines. Part 7. Hydroxylamine\u2013alkyne cyclisations. Formation of cyclic nitrones and application to the synthesis of the proposed structure for (\u00b1)-acacialactam. J. Chem. Soc. Perkin Trans. 1, 3379\u20133395.","DOI":"10.1039\/P19940003379"},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"2434","DOI":"10.1021\/ja211568k","article-title":"Reverse Cope elimination of hydroxylamines and alkenes or alkynes: Theoretical investigation of tether length and substituent effects","volume":"134","author":"Krenske","year":"2012","journal-title":"J. Am. Chem. Soc."},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"1410","DOI":"10.1002\/anie.200703495","article-title":"Intermolecular Cope-type hydroamination of alkenes and alkynes","volume":"47","author":"Beauchemin","year":"2008","journal-title":"Angew. Chem. Inter. Ed."},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"4203","DOI":"10.1039\/C4CC00493K","article-title":"Pyrroles versus cyclic nitrones: Catalyst-controlled divergent cyclization of N-(2-perfluoroalkyl-3-alkynyl) hydroxylamines","volume":"50","author":"Zeng","year":"2014","journal-title":"Chem. Commun."},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"1348","DOI":"10.1002\/adsc.201600018","article-title":"Recent advances in gold-catalyzed N- and O-functionalizations of alkynes with nitrones, nitroso, nitro and nitroxy species","volume":"358","author":"Huple","year":"2016","journal-title":"Adv. Synth. Catal."},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"1895","DOI":"10.1021\/ol900292r","article-title":"Ketonitrones via Cope-type hydroamination of allenes","volume":"11","author":"Moran","year":"2009","journal-title":"Org. Lett."},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"583","DOI":"10.1021\/jo01156a012","article-title":"Studies in the acridine series. VI. The reaction of certain 9-formylacridines with 3-dibutylaminopropylmagnesium chloride","volume":"14","author":"Perrine","year":"1949","journal-title":"J. Org. Chem."},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"2097","DOI":"10.1016\/j.tetlet.2010.11.031","article-title":"Observations on the reaction of nitronate anions with oxalyl chloride: A new method for the preparation of geminal chloronitroso compounds","volume":"52","author":"Motherwell","year":"2011","journal-title":"Tetrahedron Lett."},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"4131","DOI":"10.1021\/cr030004x","article-title":"The nitroso ene reaction:\u2009 A regioselective and stereoselective allylic nitrogen functionalization of mechanistic delight and synthetic potential","volume":"103","author":"Adam","year":"2003","journal-title":"Chem. Rev."},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"10853","DOI":"10.1039\/C4CC05044D","article-title":"An umpolung approach toward N-aryl nitrone construction: A phosphine-mediated addition of 1,2-dicarbonyls to nitroso electrophiles","volume":"50","author":"Chavannavar","year":"2014","journal-title":"Chem. Commun."},{"key":"ref_58","doi-asserted-by":"crossref","first-page":"5506","DOI":"10.1021\/acs.orglett.1c01857","article-title":"Gold catalysts can generate nitrone intermediates from a nitrosoarene\/alkene mixture, enabling two distinct catalytic reactions: A nitroso-activated cycloheptatriene\/benzylidene rearrangement","volume":"23","author":"More","year":"2021","journal-title":"Org. Lett."},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"170","DOI":"10.1002\/adsc.201801161","article-title":"An unprecedented organocascade synthesis of functionalized bicyclic nitrones from 2-aminomalonate derived nucleophiles and 1-nitro-1,3-enynes via allenes formation and subsequent rearrangement","volume":"361","author":"Huang","year":"2019","journal-title":"Adv. Synth. Cat."},{"key":"ref_60","doi-asserted-by":"crossref","first-page":"5246","DOI":"10.1021\/jacs.6b02324","article-title":"An iridium-catalyzed reductive approach to nitrones from N-hydroxyamides","volume":"138","author":"Katahara","year":"2016","journal-title":"J. Am. Chem. Soc."},{"key":"ref_61","doi-asserted-by":"crossref","first-page":"4833","DOI":"10.1021\/jo0256890","article-title":"5,5-Dimethyl-1,4,2-dioxazoles as versatile aprotic hydroxamic acid protecting groups","volume":"67","author":"Couturier","year":"2002","journal-title":"J. Org. Chem."},{"key":"ref_62","doi-asserted-by":"crossref","first-page":"10128","DOI":"10.1039\/C8CC04656E","article-title":"Synthesis of five-membered cyclic nitrones based on the Lewis acid-catalysed [3+2]-annulation reaction of donor\u2013acceptor cyclopropanes with 1,4,2-dioxazoles","volume":"54","author":"Wang","year":"2018","journal-title":"Chem. Commun."},{"key":"ref_63","doi-asserted-by":"crossref","first-page":"1263","DOI":"10.1039\/C6GC03589B","article-title":"Atom economical synthesis of N-alkylbenzamides via the iron(III) sulfate catalyzed rearrangement of 2-alkyl-3-aryloxaziridines in water and in the presence of a surfactant","volume":"19","author":"Ollevier","year":"2017","journal-title":"Green Chem."},{"key":"ref_64","doi-asserted-by":"crossref","first-page":"318","DOI":"10.1021\/ja00496a007","article-title":"Theoretical exploration of the photochemical rearrangement of oxaziridines","volume":"101","author":"Oliveros","year":"1979","journal-title":"J. Am. Chem. Soc."},{"key":"ref_65","doi-asserted-by":"crossref","first-page":"1205","DOI":"10.1021\/j100787a040","article-title":"The photochemical isomerization of \u03b1,N-diphenylnitrone","volume":"68","author":"Shinzawa","year":"1964","journal-title":"J. Phys. Chem."},{"key":"ref_66","doi-asserted-by":"crossref","first-page":"2545","DOI":"10.1021\/j100892a010","article-title":"The photochemical and thermal isomerization of trans- and cis-\u03b1-cyano-\u03b1-phenyl-N-phenylnitrones","volume":"69","author":"Koyano","year":"1965","journal-title":"J. Phys. Chem."},{"key":"ref_67","doi-asserted-by":"crossref","first-page":"1489","DOI":"10.1021\/jo01296a029","article-title":"Reactions of trans-2-tert-butyl-3-phenyloxaziridine with lithium amide bases","volume":"45","author":"Newcomb","year":"1980","journal-title":"J. Org. Chem."},{"key":"ref_68","doi-asserted-by":"crossref","first-page":"9995","DOI":"10.1039\/D1CC03855A","article-title":"Weak base-promoted selective rearrangement of oxaziridines to amides via visible-light photoredox catalysis","volume":"57","author":"Park","year":"2021","journal-title":"Chem. Commun."},{"key":"ref_69","doi-asserted-by":"crossref","first-page":"673","DOI":"10.1021\/acs.joc.5b02645","article-title":"Revealing stepwise mechanisms in dipolar cycloaddition reactions: Computational study of the reaction between nitrones and isocyanates","volume":"81","author":"Tejero","year":"2016","journal-title":"J. Org. Chem."},{"key":"ref_70","doi-asserted-by":"crossref","first-page":"3385","DOI":"10.1016\/j.tetlet.2007.03.071","article-title":"Experimental and theoretical evidences of 2-aza-Cope rearrangement of nitrones","volume":"48","author":"Merino","year":"2007","journal-title":"Tetrahedron Lett."},{"key":"ref_71","doi-asserted-by":"crossref","first-page":"45","DOI":"10.1002\/anie.198000451","article-title":"Stable 4-imino-1,2-oxazetidines from N-neopentylidene-tert-butylamine N-oxide and isocyanides","volume":"19","author":"Moderhack","year":"1980","journal-title":"Angew. Chem. Int. Ed. Eng."},{"key":"ref_72","doi-asserted-by":"crossref","first-page":"1396","DOI":"10.1021\/ar5000055","article-title":"The [3 + 3]-cycloaddition alternative for heterocycle syntheses: Catalytically generated metalloenolcarbenes as dipolar adducts","volume":"47","author":"Xu","year":"2014","journal-title":"Acc. Chem. Res."},{"key":"ref_73","doi-asserted-by":"crossref","first-page":"16402","DOI":"10.1021\/ja207664r","article-title":"Asymmetric formal [3 + 3]-cycloaddition reactions of nitrones with electrophilic vinylcarbene intermediates","volume":"133","author":"Wang","year":"2011","journal-title":"J. Am. Chem. Soc."},{"key":"ref_74","doi-asserted-by":"crossref","first-page":"3131","DOI":"10.1002\/ange.200351573","article-title":"A homo [3+2] dipolar cycloaddition: The reaction of nitrones with cyclopropanes","volume":"115","author":"Young","year":"2003","journal-title":"Angew. Chem."},{"key":"ref_75","doi-asserted-by":"crossref","first-page":"1752","DOI":"10.1139\/v05-182","article-title":"The mechanism of 1,3-dipolar cycloaddition reactions of cyclopropanes and nitrones\u2014A theoretical study","volume":"83","author":"Wanapun","year":"2005","journal-title":"Can. J. Chem."},{"key":"ref_76","doi-asserted-by":"crossref","first-page":"10251","DOI":"10.1021\/jo702073w","article-title":"Examination of homo-[3 + 2]-dipolar cycloaddition:\u2009 Mechanistic insight into regio- and diastereoselectivity","volume":"72","author":"Karadeolian","year":"2007","journal-title":"J. Org. Chem."},{"key":"ref_77","doi-asserted-by":"crossref","first-page":"1619","DOI":"10.1038\/s41467-017-01451-1","article-title":"Diastereo- and enantioselective [3 + 3] cycloaddition of spirocyclopropyl oxindoles using both aldonitrones and ketonitrones","volume":"8","author":"Xu","year":"2017","journal-title":"Nat. Commun."},{"key":"ref_78","doi-asserted-by":"crossref","first-page":"5504","DOI":"10.1002\/anie.201309886","article-title":"A new golden age for donor\u2013acceptor cyclopropanes","volume":"53","author":"Schneider","year":"2014","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_79","doi-asserted-by":"crossref","first-page":"3992","DOI":"10.1002\/ange.200604645","article-title":"Highly enantioselective and diastereoselective cycloaddition of cyclopropanes with nitrones and its application in the kinetic resolution of 2-substituted cyclopropane-1,1-dicarboxylates","volume":"119","author":"Kang","year":"2007","journal-title":"Angew. Chem."},{"key":"ref_80","doi-asserted-by":"crossref","first-page":"11420","DOI":"10.1039\/D1NJ02023D","article-title":"1,3-Dipolar cycloaddition of nitrones: Synthesis of multisubstituted, diverse range of heterocyclic compounds","volume":"45","author":"Thakur","year":"2021","journal-title":"New J. Chem."},{"key":"ref_81","doi-asserted-by":"crossref","first-page":"2355","DOI":"10.1002\/anie.202011267","article-title":"Regio- and enantioselective [3+3]-cycloaddition of nitrones with 2-indolylmethanols enabled by cooperative organocatalysis","volume":"60","author":"Li","year":"2021","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_82","doi-asserted-by":"crossref","first-page":"5901","DOI":"10.1002\/anie.200701529","article-title":"Palladium-catalyzed asymmetric [3+3]-cycloaddition of trimethylenemethane derivatives with nitrones","volume":"46","author":"Shintani","year":"2007","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_83","doi-asserted-by":"crossref","first-page":"2293","DOI":"10.1055\/s-0032-1317096","article-title":"Recent developments in nitrone chemistry: Some novel transformations","volume":"23","author":"Yang","year":"2012","journal-title":"Synlett"},{"key":"ref_84","doi-asserted-by":"crossref","first-page":"e2100081","DOI":"10.1002\/hlca.202100081","article-title":"Copper(I)-catalyzed highly enantioselective [3+3]-cycloaddition of \u03b2-aryl\/alkyl vinyl diazoacetates with nitrones","volume":"104","author":"Zheng","year":"2021","journal-title":"Helv. Chim. Acta"},{"key":"ref_85","doi-asserted-by":"crossref","first-page":"671","DOI":"10.1016\/j.tet.2016.12.034","article-title":"Unusual Lewis-acid catalyzed formal [3+3]-cycloaddition of azomethine imines and nitrones to N-vinylpyrroles","volume":"73","author":"Efremova","year":"2017","journal-title":"Tetrahedron"},{"key":"ref_86","doi-asserted-by":"crossref","first-page":"507","DOI":"10.1039\/b311200b","article-title":"1,3-Dipolar cycloaddition on solid supports: Nitrone approach towards isoxazolidines and isoxazolines and subsequent transformations","volume":"34","author":"Freysoldt","year":"2005","journal-title":"Chem. Soc. Rev."},{"key":"ref_87","doi-asserted-by":"crossref","first-page":"8825","DOI":"10.1021\/jo0513111","article-title":"The role of the sulfinyl group on the course of the reactions of 3-p-tolylsulfinylfuran-2(5H)-ones with nitrones. Synthetic uses of cycloreversion processes","volume":"70","author":"Fraile","year":"2005","journal-title":"J. Org. Chem."},{"key":"ref_88","doi-asserted-by":"crossref","first-page":"1653","DOI":"10.1021\/ol049505a","article-title":"2-tert-Butyl-3-methyl-2,3-dihydroimidazol-4-one-N-oxide:\u2009 A new nitrone-based chiral glycine equivalent","volume":"6","author":"Baldwin","year":"2004","journal-title":"Org. Lett."},{"key":"ref_89","doi-asserted-by":"crossref","first-page":"7889","DOI":"10.1016\/S0040-4039(00)74770-8","article-title":"Lewis acid-catalyzed nitrone cycloadditions to bidentate and tridentate \u03b1,\u03b2-unsaturated ketones. High rate acceleration, absolutely endo-selective and regioselective reactions","volume":"33","author":"Kanemasa","year":"1992","journal-title":"Tetrahedron Lett."},{"key":"ref_90","doi-asserted-by":"crossref","first-page":"1197","DOI":"10.1016\/j.tetasy.2009.04.002","article-title":"Asymmetric 1,3-dipolar cycloaddition reaction of \u03b1,\u03b2-unsaturated nitriles with nitrones catalyzed by chiral-at-metal rhodium or iridium complexes","volume":"20","author":"Carmona","year":"2009","journal-title":"Tetrahedron Asymmetry"},{"key":"ref_91","first-page":"767","article-title":"Synthesis and properties of azoles and their derivatives. XLIII. Regio-and stereoselectivity of [2+3] cycloaddition reaction of E-beta-nitrostyrene to Z-C-aryl-N-phenylnitrones","volume":"74","author":"Baranski","year":"2000","journal-title":"Pol. J. Chem."},{"key":"ref_92","doi-asserted-by":"crossref","first-page":"395","DOI":"10.1016\/S0040-4039(02)02502-9","article-title":"1,3-Dipolar cycloadditions of prop-1-ene-1,3-sultone with nitrile oxides\/nitrones","volume":"44","author":"Zhang","year":"2003","journal-title":"Tetrahedron Lett."},{"key":"ref_93","doi-asserted-by":"crossref","first-page":"3364","DOI":"10.1039\/C7OB00429J","article-title":"New mechanistic interpretations for nitrone reactivity","volume":"15","author":"Merino","year":"2017","journal-title":"Org. Biomol. Chem."},{"key":"ref_94","doi-asserted-by":"crossref","first-page":"2417","DOI":"10.1021\/jo052564x","article-title":"Synthesis of enantiopure indolizinones by cascade ring enlargements of 4\u2018-chlorospiro[cyclopropane-1,5\u2018-isoxazolidines]","volume":"71","author":"Revuelta","year":"2006","journal-title":"J. Org. Chem."},{"key":"ref_95","doi-asserted-by":"crossref","first-page":"10857","DOI":"10.1016\/S0040-4020(98)00628-0","article-title":"On the regioselectivity in nitrone cycloadditions to \u03b3-oxo \u03b1,\u03b2-unsaturated esters","volume":"54","author":"Figueredo","year":"1998","journal-title":"Tetrahedron"},{"key":"ref_96","doi-asserted-by":"crossref","first-page":"923","DOI":"10.1016\/S0957-4166(02)00231-8","article-title":"Catalytic enantioselective 1,3-dipolar cycloaddition of nitrones to cyclopent-1-enecarbaldehyde","volume":"13","author":"Karlsson","year":"2002","journal-title":"Tetrahedron Asymmetry"},{"key":"ref_97","doi-asserted-by":"crossref","first-page":"3253","DOI":"10.1021\/jo060348y","article-title":"Experimental and theoretical studies on stereo- and regioselectivity in intramolecular nitrone-alkene cycloaddition of hept-6-enoses derived from carbohydrates","volume":"71","author":"Shing","year":"2006","journal-title":"J. Org. Chem."},{"key":"ref_98","doi-asserted-by":"crossref","unstructured":"G\u0119barowski, P., and Sas, W. (2001). Asymmetric synthesis of novel polyhydroxylated derivatives of indolizidine and quinolizidine by intramolecular 1,3-dipolar cycloaddition of N-(3-alkenyl)nitrones. Chem. Commun., 915\u2013916.","DOI":"10.1039\/b101057n"},{"key":"ref_99","doi-asserted-by":"crossref","first-page":"1004","DOI":"10.1055\/s-1997-938","article-title":"Regio- and diastereoselectivity in the reaction sequence from secondary 3-oxa-5-hexen-1-ylamines to bicyclic compounds via nitrones","volume":"1997","author":"Aurich","year":"1997","journal-title":"Synlett"},{"key":"ref_100","doi-asserted-by":"crossref","first-page":"205","DOI":"10.1055\/s-1975-23713","article-title":"1,3-Dipolar cycloaddition reactions of nitrones","volume":"1975","author":"Black","year":"1975","journal-title":"Synthesis"},{"key":"ref_101","doi-asserted-by":"crossref","first-page":"3413","DOI":"10.1016\/S0040-4020(01)00184-3","article-title":"Synthesis of di- and cis-triaryl-3a,4,5,6-tetrahydroimidazo [1,5-b]isoxazoles and their ring-opening reactions","volume":"57","year":"2001","journal-title":"Tetrahedron"},{"key":"ref_102","doi-asserted-by":"crossref","first-page":"9167","DOI":"10.1021\/jacs.8b04635","article-title":"A revised mechanism for the Kinugasa reaction","volume":"140","author":"Malig","year":"2018","journal-title":"J. Am. Chem. Soc."},{"key":"ref_103","doi-asserted-by":"crossref","first-page":"2649","DOI":"10.1021\/jo502838p","article-title":"Theoretical study of mechanism and stereoselectivity of catalytic Kinugasa reaction","volume":"80","author":"Santoro","year":"2015","journal-title":"J. Org. Chem."},{"key":"ref_104","doi-asserted-by":"crossref","first-page":"10665","DOI":"10.1021\/acs.joc.1c01351","article-title":"Mechanism of the Kinugasa reaction revisited","volume":"86","author":"Santoro","year":"2021","journal-title":"J. Org. Chem."},{"key":"ref_105","doi-asserted-by":"crossref","first-page":"6060","DOI":"10.1021\/ja056711k","article-title":"Origin of the relative stereoselectivity of the \u03b2-lactam formation in the Staudinger reaction","volume":"128","author":"Jiao","year":"2006","journal-title":"J. Am. Chem. Soc."},{"key":"ref_106","doi-asserted-by":"crossref","first-page":"3477","DOI":"10.1021\/ol801257j","article-title":"A highly stereoselective synthesis of chiral \u03b1-amino-\u03b2-lactams via the Kinugasa reaction employing ynamides","volume":"10","author":"Zhang","year":"2008","journal-title":"Org. Lett."},{"key":"ref_107","doi-asserted-by":"crossref","first-page":"39","DOI":"10.1016\/S0022-1139(00)82735-9","article-title":"Applications of the fluorinated 1,3-dipolar compounds as the building blocks of the heterocycles with fluorine groups. Part XII. Synthesis of trifluoromethylisoxazolines and their rearrangement into trifluoromethylaziridines","volume":"39","author":"Tanaka","year":"1988","journal-title":"J. Fluorine Chem."},{"key":"ref_108","doi-asserted-by":"crossref","first-page":"27","DOI":"10.1016\/j.jfluchem.2014.05.015","article-title":"1,3-Dipolar cycloadditions of fluorinated nitrones with thioketones","volume":"165","author":"Obijalska","year":"2014","journal-title":"J. Fluorine Chem."},{"key":"ref_109","doi-asserted-by":"crossref","first-page":"112","DOI":"10.1016\/j.jfluchem.2018.05.009","article-title":"1,3-Dipolar cycloaddition in the synthesis of trifluoromethyl-substituted isoxazolidinyl derivatives of nucleobases","volume":"212","author":"Kuprianowicz","year":"2018","journal-title":"J. Fluorine Chem."},{"key":"ref_110","doi-asserted-by":"crossref","first-page":"6015","DOI":"10.1039\/C9NJ06442G","article-title":"Chemo-, regio-, and stereoselectivity in 1,3-dipolar cycloaddition of piperine with nitrones. A cycloadditive route to aminoalcohols","volume":"44","year":"2020","journal-title":"New J. Chem."},{"key":"ref_111","doi-asserted-by":"crossref","first-page":"5305","DOI":"10.1016\/j.tet.2016.06.073","article-title":"First application of fluorinated nitrones for the synthesis of fluoroalkylated \u03b2-lactams via the Kinugasa reaction","volume":"72","author":"Kowalski","year":"2016","journal-title":"Tetrahedron"},{"key":"ref_112","doi-asserted-by":"crossref","first-page":"3025","DOI":"10.1039\/c001791d","article-title":"Trifluoromethyl nitrones: From fluoral to optically active hydroxylamines","volume":"8","author":"Milcent","year":"2010","journal-title":"Org. Biomol. Chem."},{"key":"ref_113","doi-asserted-by":"crossref","first-page":"1552","DOI":"10.1246\/bcsj.36.1552","article-title":"The electronic spectra of nitrones and the solvent effect on them","volume":"36","author":"Kubota","year":"1963","journal-title":"Bull. Chem. Soc. Jpn."},{"key":"ref_114","doi-asserted-by":"crossref","first-page":"17157","DOI":"10.1021\/ja105198c","article-title":"Fast reactivity of a cyclic nitrone\u2212calix [4]pyrrole conjugate with superoxide radical anion: Theoretical and experimental studies","volume":"132","author":"Kim","year":"2010","journal-title":"J. Am. Chem. Soc."},{"key":"ref_115","doi-asserted-by":"crossref","first-page":"1646","DOI":"10.1039\/C3NR04559E","article-title":"Highly sensitive free radical detection by nitrone-functionalized gold nanoparticles","volume":"6","author":"Du","year":"2014","journal-title":"Nanoscale"},{"key":"ref_116","doi-asserted-by":"crossref","first-page":"70","DOI":"10.1016\/j.molstruc.2016.08.058","article-title":"Crystal and molecular structure studies of (Z)-N-methyl-C-4-substituted phenyl nitrones by XRD, DFT, FTIR and NMR methods","volume":"1128","author":"Lasri","year":"2017","journal-title":"J. Mol. Struct."},{"key":"ref_117","doi-asserted-by":"crossref","first-page":"120517","DOI":"10.1016\/j.molliq.2022.120517","article-title":"Dissolution of nitrones in alkylphosphates: A structural study","volume":"367","author":"Barone","year":"2022","journal-title":"J. Mol. Liq."},{"key":"ref_118","doi-asserted-by":"crossref","first-page":"16169","DOI":"10.1007\/s10853-018-2778-2","article-title":"Reducing volumetric shrinkage of photopolymerizable materials using reversible disulfide-bond reactions","volume":"53","author":"Chen","year":"2018","journal-title":"J. Mater. Sci."},{"key":"ref_119","doi-asserted-by":"crossref","unstructured":"Kaminsky, L.S., and Lamchen, M. (1968). Nitrones. Part VIII. The ultraviolet absorption of the 1-pyrroline 1-oxides. J. Chem. Soc. B: Phys. Org., 1085\u20131087.","DOI":"10.1039\/j29680001085"},{"key":"ref_120","doi-asserted-by":"crossref","first-page":"993","DOI":"10.1021\/ma4025174","article-title":"UV\u2013Vis monitoring of radical polymerizations by spin trapping with chromophoric nitrones","volume":"47","author":"Husmann","year":"2014","journal-title":"Macromolecules"},{"key":"ref_121","doi-asserted-by":"crossref","first-page":"276","DOI":"10.1016\/j.jphotochem.2005.06.007","article-title":"Fluorescence self-quenching of substituted N,\u03b1-diphenylnitrones in various solvents","volume":"177","author":"Khoee","year":"2006","journal-title":"J. Photochem. Photobiol. A Chem."},{"key":"ref_122","doi-asserted-by":"crossref","first-page":"110815","DOI":"10.1016\/j.optmat.2021.110815","article-title":"The optical nonlinear properties of a new synthesized azo-nitrone compound","volume":"113","author":"Mutlaq","year":"2021","journal-title":"Opt. Mater."},{"key":"ref_123","doi-asserted-by":"crossref","first-page":"916","DOI":"10.1021\/j100445a026","article-title":"Spin trapping in electrochemistry. 2. Aqueous and nonaqueous electrochemical characterizations of spin traps","volume":"84","author":"McIntire","year":"1980","journal-title":"J. Phys. Chem."},{"key":"ref_124","doi-asserted-by":"crossref","first-page":"1171","DOI":"10.4155\/fmc.12.74","article-title":"Potential implication of the chemical properties and bioactivity of nitrone spin traps for therapeutics","volume":"4","author":"Villamena","year":"2012","journal-title":"Future Med. Chem."},{"key":"ref_125","doi-asserted-by":"crossref","first-page":"3572","DOI":"10.1016\/j.bmc.2007.02.033","article-title":"\u03b1-Phenyl-N-tert-butyl nitrone (PBN) derivatives: Synthesis and protective action against microvascular damages induced by ischemia\/reperfusion","volume":"15","author":"Kim","year":"2007","journal-title":"Bioorganic Med. Chem."},{"key":"ref_126","doi-asserted-by":"crossref","unstructured":"Rizzi, C., Marque, S., Belin, F., Bouteiller, J.C., Lauricella, R., Tuccio, B., Cerri, V., and Tordo, P. (1997). PPN-type nitrones: Preparation and use of a new series of \u03b2-phosphorylated spin-trapping agents. J. Chem. Soc. Perkin Trans. 2, 2513\u20132518.","DOI":"10.1039\/a702469j"},{"key":"ref_127","doi-asserted-by":"crossref","first-page":"2165","DOI":"10.1021\/jm991154w","article-title":"Synthesis, structure, and neuroprotective properties of novel imidazolyl nitrones","volume":"43","author":"Dhainaut","year":"2000","journal-title":"J. Med. Chem."},{"key":"ref_128","doi-asserted-by":"crossref","first-page":"3097","DOI":"10.1074\/jbc.271.6.3097","article-title":"Characterization of the radical trapping Activity of a novel series of cyclic nitrone spin traps","volume":"271","author":"Thomas","year":"1996","journal-title":"J. Biol. Chem."},{"key":"ref_129","doi-asserted-by":"crossref","first-page":"259","DOI":"10.1016\/0891-5849(89)90133-0","article-title":"Sonochemistry of nitrone spin traps in aqueous solutions. Evidence for pyrolysis radicals from spin traps","volume":"7","author":"Kondo","year":"1989","journal-title":"Free Radic. Biol. Med."},{"key":"ref_130","unstructured":"(2025, November 17). Wikiwand\u2014Biological Functions of Nitric Oxide. Available online: https:\/\/www.wikiwand.com\/en\/Biological_functions_of_nitric_oxide."},{"key":"ref_131","doi-asserted-by":"crossref","first-page":"3220","DOI":"10.1039\/b507530k","article-title":"Nitric oxide release from the unimolecular decomposition of the superoxide radical anion adduct of cyclic nitrones in aqueous medium","volume":"3","author":"Locigno","year":"2005","journal-title":"Org. Biomol. Chem."},{"key":"ref_132","doi-asserted-by":"crossref","first-page":"1361","DOI":"10.1016\/j.freeradbiomed.2008.08.017","article-title":"Nitrones as therapeutics","volume":"45","author":"Floyd","year":"2008","journal-title":"Free Radic. Biol. Med."},{"key":"ref_133","doi-asserted-by":"crossref","first-page":"321","DOI":"10.3109\/10715768609080971","article-title":"Phenyl-t-butyl-nitrone is active against traumatic shock in rats","volume":"1","author":"Novelli","year":"1986","journal-title":"Free Radic. Res. Commun."},{"key":"ref_134","doi-asserted-by":"crossref","first-page":"2158","DOI":"10.1016\/j.jstrokecerebrovasdis.2018.03.015","article-title":"NXY-059, a failed stroke neuroprotectant, offers no protection to stem cell-derived human neurons","volume":"27","author":"Antonic","year":"2018","journal-title":"J. Stroke Cerebrovasc. Dis."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/31\/1\/13\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,12,26]],"date-time":"2025-12-26T05:15:09Z","timestamp":1766726109000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/31\/1\/13"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2025,12,19]]},"references-count":134,"journal-issue":{"issue":"1","published-online":{"date-parts":[[2026,1]]}},"alternative-id":["molecules31010013"],"URL":"https:\/\/doi.org\/10.3390\/molecules31010013","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2025,12,19]]}}}