{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,25]],"date-time":"2026-09-25T14:02:43Z","timestamp":1790344963985,"version":"4.1.0"},"reference-count":33,"publisher":"American Chemical Society (ACS)","issue":"38","license":[{"start":{"date-parts":[[2026,9,16]],"date-time":"2026-09-16T00:00:00Z","timestamp":1789516800000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-029"},{"start":{"date-parts":[[2026,9,16]],"date-time":"2026-09-16T00:00:00Z","timestamp":1789516800000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-037"},{"start":{"date-parts":[[2026,9,16]],"date-time":"2026-09-16T00:00:00Z","timestamp":1789516800000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-045"}],"funder":[{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["22671116"],"award-info":[{"award-number":["22671116"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100013314","name":"Higher Education Discipline Innovation Project","doi-asserted-by":"publisher","award":["BC2018061"],"award-info":[{"award-number":["BC2018061"]}],"id":[{"id":"10.13039\/501100013314","id-type":"DOI","asserted-by":"publisher"}]},{"name":"Fujian Province","award":["3502ZCQXT2021006"],"award-info":[{"award-number":["3502ZCQXT2021006"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2026,9,25]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>A mild and efficient photoinduced radical cascade cyclization strategy that enables the introduction of a Br atom and the construction of the pyrazolone scaffold from N-methacryloyl hydrazones with tetrabutylammonium bromide (TBAB) has been developed. This transformation employs cheap and readily available TBAB as the bromine source through in situ generation of key radical species, followed by a 5-endo-trig cyclization. This protocol features excellent functional group tolerance and a broad substrate scope and could be successfully applied to the late-stage modification of drug molecules, highlighting its practical utility.<\/jats:p>","DOI":"10.1021\/acs.joc.6c01587","type":"journal-article","created":{"date-parts":[[2026,9,16]],"date-time":"2026-09-16T18:02:33Z","timestamp":1789581753000},"page":"13008-13012","source":"Crossref","is-referenced-by-count":0,"title":["Visible-Light-Promoted\nBromocyclization of\n                    <i>N<\/i>\n                    -Methacryloyl Hydrazones\nfor the Synthesis of Brominated\nPyrazolones"],"prefix":"10.1021","volume":"91","author":[{"given":"Gang","family":"Yang","sequence":"first","affiliation":[{"name":"Huaqiao University , , , ; orcid.org\/0000-0001-5759-766X","place":["Xiamen, P. R. China, 361021"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Hong","family":"Zhang","sequence":"additional","affiliation":[{"name":"Huaqiao University , , , ; orcid.org\/0000-0001-5759-766X","place":["Xiamen, P. R. China, 361021"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5759-766X","authenticated-orcid":true,"given":"Xiuling","family":"Cui","sequence":"additional","affiliation":[{"name":"Huaqiao University , , , ; orcid.org\/0000-0001-5759-766X","place":["Xiamen, P. R. China, 361021"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,9,16]]},"reference":[{"key":"2026092509092617500_cit1a","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202407983","article-title":"Isothiourea-Catalysed Acylative Kinetic\nResolution of Tertiary Pyrazolone Alcohols","volume":"63","author":"Westwood","year":"2024","journal-title":"Angew. Chem. Int. Ed."},{"key":"2026092509092617500_cit1b","doi-asserted-by":"publisher","first-page":"433","DOI":"10.1021\/acs.orglett.4c04395","article-title":"Stereoselective Divergent\nSynthesis of Chiral Pyrazolone Derivatives via Multicomponent\nCascade Reactions by Isothiourea Catalysis","volume":"27","author":"Liu","year":"2025","journal-title":"Org. Lett."},{"key":"2026092509092617500_cit1c","doi-asserted-by":"publisher","first-page":"4852","DOI":"10.1039\/D5QO00499C","article-title":"Enantioselective and\ndiastereodivergent construction of oxindole\u2013pyrazolone conjugates\nbearing an alkenyl substituted quaternary chlorinated stereogenic\ncentre","volume":"12","author":"Chen","year":"2025","journal-title":"Org. Chem. Front."},{"key":"2026092509092617500_cit1d","doi-asserted-by":"publisher","first-page":"2601","DOI":"10.1021\/jm010032c","article-title":"The Effect\nof 1,3-Diaryl-[1H]-pyrazole-4-acetamides on Glucose\nUtilization in ob\/ob Mice","volume":"44","author":"Bebernitz","year":"2001","journal-title":"J. Med. Chem."},{"key":"2026092509092617500_cit1e","doi-asserted-by":"publisher","first-page":"14783","DOI":"10.1039\/D5GC02947C","article-title":"Site-selective electrochemical C(sp3)\u2013H late-stage functionalization of pyrazolones","volume":"27","author":"Zhang","year":"2025","journal-title":"Green Chem."},{"key":"2026092509092617500_cit1f","doi-asserted-by":"publisher","first-page":"1582","DOI":"10.3390\/molecules30071582","article-title":"The Role of Flow\nChemistry on the Synthesis of Pyrazoles, Pyrazolines and Pyrazole-Fused\nScaffolds","volume":"30","author":"Correia","year":"2025","journal-title":"Molecules"},{"key":"2026092509092617500_cit1g","doi-asserted-by":"publisher","first-page":"135103","DOI":"10.1016\/j.gresc.2025.03.009","article-title":"Advances in pyrazolone\nfunctionalization: A review since 2020","volume":"192","author":"Liao","year":"2026","journal-title":"Tetrahedron"},{"key":"2026092509092617500_cit1h","doi-asserted-by":"publisher","first-page":"112959","DOI":"10.1016\/j.cclet.2026.112959","article-title":"Atom-economical hydroalkylation of oxyallenes with\npyrazolones enabled by molybdenum catalysis","author":"Fan","year":"2026","journal-title":"Chin. Chem. Lett."},{"key":"2026092509092617500_cit1i","doi-asserted-by":"publisher","first-page":"110114","DOI":"10.1016\/j.cclet.2024.110114","article-title":"Copper-catalyzed asymmetric\n[4+1] annulation of yne-allylic esters with pyrazolones","volume":"36","author":"Xu","year":"2025","journal-title":"Chin. Chem. Lett."},{"key":"2026092509092617500_cit1j","doi-asserted-by":"publisher","first-page":"102","DOI":"10.1016\/j.gresc.2021.11.004","article-title":"Visible light-promoted enantioselective aerobic oxidation of pyrazolones\nby phase transfer catalysis","volume":"3","author":"Wang","year":"2022","journal-title":"Green Synth. Catal."},{"key":"2026092509092617500_cit1k","doi-asserted-by":"publisher","first-page":"267","DOI":"10.6023\/cjoc202406005","article-title":"N. Heterocyclic\nCarbene-Catalyzed [4+2] Cycloaddition of Salicylaldehydes with Pyrazole-4,5-diones\nfor the Synthesis of Spiroketal-Pyrazolones","volume":"45","author":"Wang","year":"2025","journal-title":"Chin. J. Org. Chem."},{"key":"2026092509092617500_cit2a","doi-asserted-by":"publisher","first-page":"2675","DOI":"10.1021\/ol060570p","article-title":"1,3-Diketones\nfrom Acid Chlorides\nand Ketones: A Rapid and General One-Pot Synthesis of Pyrazoles","volume":"8","author":"Heller","year":"2006","journal-title":"Org. Lett."},{"key":"2026092509092617500_cit2b","doi-asserted-by":"publisher","first-page":"4491","DOI":"10.1021\/ol701961z","article-title":"SmCl3-Catalyzed C-Acylation of 1,3-Dicarbonyl Compounds and Malononitrile","volume":"9","author":"Shen","year":"2007","journal-title":"Org. Lett."},{"key":"2026092509092617500_cit2c","doi-asserted-by":"publisher","first-page":"1729","DOI":"10.1007\/s11164-015-2114-2","article-title":"One-pot multicomponent\nsynthesis of novel 1-thiazolyl-5-coumarin-3-yl-pyrazole derivatives\nand evaluation of their cytotoxic activity","volume":"42","author":"Velpula","year":"2016","journal-title":"Res. Chem. Intermed."},{"key":"2026092509092617500_cit2d","doi-asserted-by":"publisher","first-page":"4138","DOI":"10.1039\/D5OB01676B","article-title":"Visible light-driven\nstrategies for the synthesis of pyrazole scaffolds: needs, mechanistic\ninsights and sustainable horizons","volume":"24","author":"Nisha","year":"2026","journal-title":"Org. Biomol.\nChem."},{"key":"2026092509092617500_cit3","doi-asserted-by":"publisher","first-page":"66","DOI":"10.1021\/acsbiomedchemau.4c00060","article-title":"Antimicrobial Efficacy\nof 1,2,3-Triazole-Incorporated Indole-Pyrazolone against Drug-Resistant\nESKAPE Pathogens: Design and Synthesis","volume":"5","author":"Upadhyay","year":"2025","journal-title":"ACS\nBio Med Chem Au"},{"key":"2026092509092617500_cit4a","doi-asserted-by":"publisher","first-page":"13907","DOI":"10.1039\/D4CC05086J","article-title":"Photoredox-catalyzed\narylative and aryl sulfonylative radical cascades involving diaryliodonium\nreagents: synthesis of functionalized pyrazolones","volume":"60","author":"Thombare","year":"2024","journal-title":"Chem. Commun."},{"key":"2026092509092617500_cit4b","doi-asserted-by":"publisher","first-page":"3667","DOI":"10.1021\/acs.orglett.4c01176","article-title":"Photodecarboxylative Radical Cascade Involving N-(Acyloxy)phthalimides for the Synthesis of Pyrazolones","volume":"26","author":"Panda","year":"2024","journal-title":"Org. Lett."},{"key":"2026092509092617500_cit5","doi-asserted-by":"publisher","first-page":"1805","DOI":"10.1021\/acs.joc.5c03039","article-title":"Visible\nLight-Induced Cyclization of N-Arylmethacrylohydrazides\nand Hydroxamic Acid Derivatives toward\n\u03b4-Amidoalkylated Pyrazol-5-ones via 1,5-Hydrogen\nAtom Transfer","volume":"91","author":"Cheng","year":"2026","journal-title":"J. Org. Chem."},{"key":"2026092509092617500_cit6","doi-asserted-by":"publisher","first-page":"1196","DOI":"10.1039\/D4CC05976J","article-title":"Access to 1-aryl-pyrazolin-5-ones via photoinduced chemoselective cyclization of N-methacrylo aldehyde hydrazones","volume":"61","author":"Yu","year":"2025","journal-title":"Chem. Commun."},{"key":"2026092509092617500_cit7","doi-asserted-by":"publisher","first-page":"11982","DOI":"10.1021\/acs.joc.5c01659","article-title":"Dual Role of Trifluoromethyl Thianthrenium\nTriflate in Self-Catalyzed Phototandem Trifluoromethyl\/Cyclization\nof N-Methacryloyl Aldehyde Hydrazones in EtOH","volume":"90","author":"Liu","year":"2025","journal-title":"J. Org. Chem."},{"key":"2026092509092617500_cit8","doi-asserted-by":"publisher","first-page":"4619","DOI":"10.1021\/acs.joc.5c03037","article-title":"Radical Azidation\/Cyclization Cascade of N-Acrylohydrazides: Access to Biologically Relevant Azido-Pyrazolones","volume":"91","author":"Nishad","year":"2026","journal-title":"J. Org. Chem."},{"key":"2026092509092617500_cit9","doi-asserted-by":"publisher","first-page":"248","DOI":"10.1021\/acs.orglett.5c04624","article-title":"Photochemical Construction\nof Trifluoromethyl Bicyclo[1.1.1]pentyl-heterocycles","volume":"28","author":"Gil-Ordo\u0301n\u0303ez","year":"2026","journal-title":"Org. Lett."},{"key":"2026092509092617500_cit10","doi-asserted-by":"publisher","first-page":"9457","DOI":"10.1021\/acs.joc.5c00861","article-title":"Access to\n1-Aryl-pyrazolin-5-ones via Photocatalytic Chemoselective\nTri\/Difluoromethylation\nand Cyclization of N-Methacryloyl Aldehyde Hydrazones","volume":"90","author":"Pan","year":"2025","journal-title":"J. Org. Chem."},{"key":"2026092509092617500_cit11","doi-asserted-by":"publisher","first-page":"214404","DOI":"10.1016\/j.ccr.2021.214404","article-title":"Recent development\nof biomimetic halogenation inspired by vanadium dependent haloperoxidase","volume":"457","author":"Chen","year":"2022","journal-title":"Coord. Chem. Rev."},{"key":"2026092509092617500_cit12a","doi-asserted-by":"publisher","first-page":"0077","DOI":"10.1038\/s41570-017-0077","article-title":"Radical\ncascade reactions triggered by single electron transfer","volume":"1","author":"Plesniak","year":"2017","journal-title":"Nat. Rev. Chem."},{"key":"2026092509092617500_cit12b","doi-asserted-by":"publisher","first-page":"4626","DOI":"10.1039\/C8CS00947C","article-title":"Catalytic cascade reactions by radical relay","volume":"48","author":"Huang","year":"2019","journal-title":"Chem. Soc. Rev."},{"key":"2026092509092617500_cit13","doi-asserted-by":"publisher","first-page":"2134","DOI":"10.1021\/acs.joc.5c02792","article-title":"Radical Bromocyclization\nof Alkynes for the Synthesis of Thio-Flavonoids and Benzothiophenes","volume":"91","author":"Yang","year":"2026","journal-title":"J. Org. Chem."},{"key":"2026092509092617500_cit14a","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.70349","article-title":"Photoinduced Tandem Cyclization of\nUnsaturated Aldehyde Hydrazones with N-Amidopyridinium\nSalts to Access Amidated Pyrazolones","volume":"368","author":"Zeng","year":"2026","journal-title":"Adv. Synth.\nCatal."},{"key":"2026092509092617500_cit14b","doi-asserted-by":"publisher","first-page":"17907","DOI":"10.1021\/acs.joc.5c02447","article-title":"Visible-Light-Induced Perfluoroalkylation\/Cyclization to Access Perfluoroalkylated\nPyrazol-5-ones via Halogen-Bond-Based Electron Donor\u2013Acceptor\n(EDA) Complexes","volume":"90","author":"Yu","year":"2025","journal-title":"J. Org. Chem."},{"key":"2026092509092617500_cit14c","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.70118","article-title":"Photoredox-Catalyzed\nSynthesis of a Novel Class of Fluoroalkyl Pyrazolones","volume":"367","author":"Pissinati","year":"2025","journal-title":"Adv. Synth. Catal."},{"key":"2026092509092617500_cit15a","doi-asserted-by":"publisher","first-page":"20713","DOI":"10.1039\/D3NJ04433E","article-title":"Photo-promoted cascade cyclization\nof aryl alkynes: access to thiocyanate\/trifluoromethylthio-containing\nquinolino[2,1-b]quinazolinones","volume":"47","author":"Fan","year":"2023","journal-title":"New J. Chem."},{"key":"2026092509092617500_cit15b","doi-asserted-by":"publisher","first-page":"7228","DOI":"10.1039\/D4CC01970A","article-title":"Visible-light-induced photocatalyst-free cascade cyclization\nof 3-(2-(ethynyl)phenyl)quinazolinones to sulfonated quinolino[2,1-b]quinazolinones","volume":"60","author":"Zeng","year":"2024","journal-title":"Chem. Commun."}],"container-title":["The Journal of Organic Chemistry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/acs.joc.6c01587","content-type":"application\/pdf","content-version":"vor","intended-application":"unspecified"},{"URL":"https:\/\/pubs.acs.org\/joceah\/article-pdf\/91\/38\/13008\/68536320\/acs.joc.6c01587.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"https:\/\/pubs.acs.org\/joceah\/article-pdf\/91\/38\/13008\/68536320\/acs.joc.6c01587.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,9,25]],"date-time":"2026-09-25T13:32:15Z","timestamp":1790343135000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/joceah\/article\/91\/38\/13008\/5431577\/Visible-Light-Promoted-Bromocyclization-of-N"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,9,16]]},"references-count":33,"journal-issue":{"issue":"38","published-online":{"date-parts":[[2026,9,16]]},"published-print":{"date-parts":[[2026,9,25]]}},"URL":"https:\/\/doi.org\/10.1021\/acs.joc.6c01587","relation":{},"ISSN":["0022-3263","1520-6904"],"issn-type":[{"value":"0022-3263","type":"print"},{"value":"1520-6904","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,9,16]]}}}