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The one-pot reactions involving (N-isocyanimine)triphenylphosphorane, tertiary amines, and carboxylic acids resulted in the formation of 1,3,4-oxadiazoles in moderate to good yields through a consecutive oxidative Ugi\/aza-Wittig reaction, enabling the direct functionalization of sp3 C-H bonds adjacent to the nitrogen atom. This method offered several notable advantages, including ligands-free, exceptional productivity and a high functional group tolerance. The preliminary biological evaluation demonstrated that compound 4f inhibited hepatoma cells efficiently, suggesting potentially broad applications of the approach for synthesis and medicinal chemistry.<\/jats:p>","DOI":"10.3390\/molecules29061253","type":"journal-article","created":{"date-parts":[[2024,3,12]],"date-time":"2024-03-12T03:55:34Z","timestamp":1710215734000},"page":"1253","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":8,"title":["One-Step Construction of 1,3,4-Oxadiazoles with Anticancer Activity from Tertiary Amines via a Sequential Copper(I)-Catalyzed Oxidative Ugi\/aza-Wittig Reaction"],"prefix":"10.3390","volume":"29","author":[{"ORCID":"https:\/\/orcid.org\/0009-0001-4590-1465","authenticated-orcid":false,"given":"Mei","family":"Sun","sequence":"first","affiliation":[{"name":"Anhui Key Laboratory of Low Temperature Co-Fired Materials, School of Chemistry and Material Engineering, Huainan Normal University, Huainan 232038, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Nong-Qi","family":"Mao","sequence":"additional","affiliation":[{"name":"School of Pharmacy, Xianning Medical College, Hubei University of Science and Technology, Xianning 437100, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Sheng-Long","family":"Wang","sequence":"additional","affiliation":[{"name":"School of Pharmacy, Xianning Medical College, Hubei University of Science and Technology, Xianning 437100, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xin-Ming","family":"Han","sequence":"additional","affiliation":[{"name":"School of Pharmacy, Xianning Medical College, Hubei University of Science and Technology, Xianning 437100, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Gang","family":"Yao","sequence":"additional","affiliation":[{"name":"School of Pharmacy, Xianning Medical College, Hubei University of Science and Technology, Xianning 437100, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ping","family":"Xue","sequence":"additional","affiliation":[{"name":"School of Pharmacy, Xianning Medical College, Hubei University of Science and Technology, Xianning 437100, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Chong-Yang","family":"Zeng","sequence":"additional","affiliation":[{"name":"Anhui Key Laboratory of Low Temperature Co-Fired Materials, School of Chemistry and Material Engineering, Huainan Normal University, Huainan 232038, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yu-Ting","family":"Liu","sequence":"additional","affiliation":[{"name":"Anhui Key Laboratory of Low Temperature Co-Fired Materials, School of Chemistry and Material Engineering, Huainan Normal University, Huainan 232038, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Kai","family":"Chen","sequence":"additional","affiliation":[{"name":"Anhui Key Laboratory of Low Temperature Co-Fired Materials, School of Chemistry and Material Engineering, Huainan Normal University, Huainan 232038, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xiao-Qing","family":"Gao","sequence":"additional","affiliation":[{"name":"Anhui Key Laboratory of Low Temperature Co-Fired Materials, School of Chemistry and Material Engineering, Huainan Normal University, Huainan 232038, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jun","family":"Xiong","sequence":"additional","affiliation":[{"name":"School of Pharmacy, Xianning Medical College, Hubei University of Science and Technology, Xianning 437100, China"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2024,3,12]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"2670","DOI":"10.1021\/jo400023z","article-title":"Unexpected Formation of N-(1-(2-Aryl-hydrazono)isoindolin-2-yl)benzamides and Their Conversion into 1,2-(Bis-1,3,4-oxadiazol-2-yl)benzenes","volume":"78","author":"Paraschivescu","year":"2013","journal-title":"J. Org. Chem."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"110","DOI":"10.1016\/j.dyepig.2014.10.018","article-title":"Blue Light-Emitting Polyamide and Poly(amide-imide)s Containing 1,3,4-Oxadiazole Ring in the Side Chain","volume":"114","author":"Hamciuc","year":"2015","journal-title":"Dye. Pigment."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"91","DOI":"10.1016\/j.ejmech.2013.05.024","article-title":"Synthesis and Biological Screening of 5-(Alkyl(1H-Indol-3-yl))-2-(Substituted)-1,3,4-Oxadiazoles as Antiproliferative and Anti-Inflammatory Agents","volume":"66","author":"Rapolu","year":"2013","journal-title":"Eur. J. Med. Chem."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"5497","DOI":"10.1002\/anie.202014207","article-title":"1,3,4-Oxadiazole Bridges: A Strategy to Improve Energetics at the Molecular Level","volume":"60","author":"Ma","year":"2020","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"789","DOI":"10.2174\/138955712801264800","article-title":"1,3,4-Oxadiazole: A Biologically Active Scaffold","volume":"12","author":"Khalilullah","year":"2012","journal-title":"Mini Rev. Med. Chem."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"572","DOI":"10.1111\/cbdd.13795","article-title":"1,3,4-oxadiazole and its Derivatives: A Review on Recent Progress in Anticancer Activities","volume":"97","author":"Vaidya","year":"2021","journal-title":"Chem. Biol. Drug Des."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"443","DOI":"10.7164\/antibiotics.24.443","article-title":"In Vitro Sensitivity of Mycoplasmas Isolated from Various Animals and Sewage to Antibiotics and Nitrofurans","volume":"24","author":"Ogata","year":"1971","journal-title":"J. Antibiot."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"1168","DOI":"10.1002\/jps.2600721015","article-title":"Determinations of Tiodazosin and Levulinic Acid from Tablets by High-Performance Liquid Chromatography","volume":"72","author":"Prosser","year":"1983","journal-title":"J. Pharm. Sci."},{"key":"ref_9","first-page":"3789","article-title":"Target Identification of a Novel Unsymmetrical 1,3,4-Oxadiazole Derivative with Antiproliferative Properties","volume":"236","author":"Dong","year":"2020","journal-title":"J. Cell Physiol."},{"key":"ref_10","first-page":"1869","article-title":"1,3,4-Oxadiazoles as Telomerase Inhibitor: Potential Anticancer Agents","volume":"17","author":"Shalini","year":"2017","journal-title":"Anti-Cancer Agents Med. Chem."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"4193","DOI":"10.1016\/j.bmcl.2003.07.018","article-title":"The Synthesis and Antibacterial Activity of 1,3,4-Thiadiazole Phenyl Oxazolidinone Analogues","volume":"13","author":"Thomasco","year":"2003","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_12","doi-asserted-by":"crossref","unstructured":"Kashid, B.B., Salunkhe, P.H., Dongare, B.B., More, K.R., Khedkar, V.A., and Ghanwat, A.A. (2020). Synthesis of Novel of 2,5-Disubstituted 1,3,4-Oxadiazole Derivatives and Their in Vitro Anti-Inflammatory, Anti-Oxidant Evaluation, and Molecular Docking Study. Bioorg. Med. Chem. Lett., 30.","DOI":"10.1016\/j.bmcl.2020.127136"},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"2960","DOI":"10.1021\/acs.orglett.5b01241","article-title":"Direct Annulation of Hydrazides to 1,3,4-Oxadiazoles via Oxidative C(CO)\u2013C(Methyl) Bond Cleavage of Methyl Ketones","volume":"17","author":"Gao","year":"2015","journal-title":"Org. Lett."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"7320","DOI":"10.1021\/acs.orglett.9b02614","article-title":"1,3,4-Oxadiazoles by Ugi-Tetrazole and Huisgen Reaction","volume":"21","author":"Wang","year":"2019","journal-title":"Org. Lett."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"279","DOI":"10.1002\/ajoc.201800684","article-title":"Facile Synthesis of Unsymmetrical 2,5-Disubstituted 1,3,4-Oxadiazoles by the Cyclization of Gem-Difluoroalkenes with Acyl Hydrazides","volume":"8","author":"Zhang","year":"2019","journal-title":"Asian J. Org. Chem."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"8209","DOI":"10.1021\/acs.orglett.1c02945","article-title":"A Three-Component Ugi-Type Reaction of N-Carbamoyl Imines Enables a Broad Scope Primary \u03b1-Amino 1,3,4-Oxadiazole Synthesis","volume":"23","author":"Boulter","year":"2021","journal-title":"Org. Lett."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"3469","DOI":"10.1002\/adsc.201500778","article-title":"Palladium-Catalyzed Aminocarbonylation Reaction to Access 1,3,4-Oxadiazoles using Chloroform as the Carbon Monoxide Source","volume":"357","author":"Wang","year":"2015","journal-title":"Adv. Synth. Catal."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"3986","DOI":"10.1002\/adsc.201900395","article-title":"DMF as Methine Source: Copper-Catalyzed Direct Annulation of Hydrazides to 1,3,4-Oxadiazoles","volume":"361","author":"Wang","year":"2019","journal-title":"Adv. Synth. Catal."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"12498","DOI":"10.1021\/acs.joc.2c01669","article-title":"A One-Pot Synthesis-Functionalization Strategy for Streamlined Access to 2,5-Disubstituted 1,3,4-Oxadiazoles from Carboxylic Acids","volume":"87","author":"Dixon","year":"2022","journal-title":"J. Org. Chem."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"4921","DOI":"10.1039\/C9CS00086K","article-title":"Catalytic alkylation of unactivated C(sp3)-H bonds for C(sp3)-C(sp3) bond formation","volume":"48","author":"Chen","year":"2019","journal-title":"Chem. Soc. Rev."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"11810","DOI":"10.1021\/ja0460763","article-title":"CuBr-Catalyzed Efficient Alkynylation of sp3 C-H Bonds Adjacent to a Nitrogen Atom","volume":"126","author":"Li","year":"2004","journal-title":"J. Am. Chem. Soc."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"6968","DOI":"10.1021\/ja0516054","article-title":"CuBr-Catalyzed Direct Indolation of Tetrahydroisoquinolines via Cross-Dehydrogenative Coupling between sp3 C-H and sp2 C-H Bonds","volume":"127","author":"Li","year":"2005","journal-title":"J. Am. Chem. Soc."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"1259","DOI":"10.1039\/C6QO00249H","article-title":"Versatile and Highly Efficient Oxidative C(sp3)-H Bond Functionalization of Tetrahydroisoquinoline Promoted by Bifunctional Diethyl Azodicarboxylate (DEAD): Scope and Mechanistic Insights","volume":"3","author":"Suga","year":"2016","journal-title":"Org. Chem. Front."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"3723","DOI":"10.1039\/D2QO00562J","article-title":"Cobalt-Catalyzed C(sp3)\u2013H Bond Functionalization to Access Indole Derivatives","volume":"9","author":"Zhang","year":"2020","journal-title":"Org. Chem. Front."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"5588","DOI":"10.1039\/c2cs35096c","article-title":"From C(sp2)\u2013H to C(sp3)\u2013H: Systematic studies on transition metal-catalyzed oxidative C\u2013C formation","volume":"41","author":"Li","year":"2012","journal-title":"Chem. Soc. Rev."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"1627","DOI":"10.1039\/C7CC09872C","article-title":"Iron-Catalyzed C(sp3)\u2212H Functionalization of N,N-Dimethylanilines with Isocyanides","volume":"54","author":"Guerrero","year":"2018","journal-title":"Chem. Commun."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"6234","DOI":"10.1002\/anie.201006515","article-title":"Multicomponent Reaction Design in the Quest for Molecular Complexity and Diversity","volume":"50","author":"Ruijter","year":"2011","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"5235","DOI":"10.1021\/cr900411f","article-title":"Isocyanoacetate Derivatives: Synthesis, Reactivity, and Application","volume":"110","author":"Gulevich","year":"2010","journal-title":"Chem. Rev."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"7085","DOI":"10.1021\/acs.joc.2c00244","article-title":"Highly Stereoselective Ugi\/Pictet-Spengler Sequence","volume":"87","author":"Zhang","year":"2022","journal-title":"J. Org. Chem."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"2343","DOI":"10.1021\/acs.joc.3c02314","article-title":"Synthesis of Benzoxazines by Heterogeneous Multicomponent Biochemo Multienzymes Cascade Reaction","volume":"89","author":"Tomaino","year":"2024","journal-title":"J. Org. Chem."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"15197","DOI":"10.1021\/acs.joc.2c01724","article-title":"I2-Promoted in Situ Cyclization\u2013Rethiolation Reaction: Synthesis of 2-Aliphatic- or Aromatic-Substituted Indolizines","volume":"87","author":"Zhao","year":"2022","journal-title":"J. Org. Chem."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"5983","DOI":"10.1039\/D2QO01130A","article-title":"One-pot and divergent synthesis of polysubstituted quinolin-2(1H)-ones and oxireno[2,3-c]quinolin-2(1aH,3H,7bH)-ones via sequential Ugi\/Knoevenagel condensation\/hydrolysis and Ugi\/Corey\u2013Chaykovsky epoxidation reactions","volume":"9","author":"Yang","year":"2022","journal-title":"Org. Chem. Front."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"4084","DOI":"10.1002\/adsc.202000736","article-title":"A Decarboxylative C(sp3)-N Bond Forming Reaction to Construct 4-Imidazolidinones via Post-Ugi Cascade Sequence in One Pot","volume":"362","author":"Song","year":"2020","journal-title":"Adv. Synth. Catal."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"4568","DOI":"10.1021\/ol9018166","article-title":"Highly Efficient Oxidation of Amines to Imines by Singlet Oxygen and Its Application in Ugi-Type Reactions","volume":"11","author":"Jiang","year":"2009","journal-title":"Org. Lett."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"5285","DOI":"10.1021\/acs.joc.7b00594","article-title":"Metal-Free Organocatalytic Oxidative Ugi Reaction Promoted by Hypervalent Iodine","volume":"82","author":"Singh","year":"2017","journal-title":"J. Org. Chem."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"11562","DOI":"10.1021\/acs.joc.9b01422","article-title":"2,4,6-Trihydroxybenzoic Acid-Catalyzed Oxidative Ugi Reactions with Molecular Oxygen via Homo- and Cross-Coupling of Amines","volume":"84","author":"Dong","year":"2019","journal-title":"J. Org. Chem."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"5775","DOI":"10.1002\/anie.200701603","article-title":"IBX-Mediated Oxidative Ugi-Type Multicomponent Reactions: Application to the N and C1 Functionalization of Tetrahydroisoquinoline","volume":"46","author":"Ngouansavanh","year":"2007","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"4240","DOI":"10.1021\/ol101576q","article-title":"Copper-Catalyzed Synthesis of \u03b1-Amino Imides from Tertiary Amines: Ugi-Type Three-Component Assemblies Involving Direct Functionalization of sp3 C-Hs Adjacent to Nitrogen Atoms","volume":"12","author":"Ye","year":"2010","journal-title":"Org. Lett."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"6338","DOI":"10.1002\/ejoc.201701323","article-title":"DEAD-Promoted Oxidative Ugi-Type Reaction Including an Unprecedented Ugi Amidation Assisted by Dicarboxylic Acids","volume":"2017","author":"Wang","year":"2017","journal-title":"Eur. J. Org. Chem."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"409","DOI":"10.1055\/s-0031-1290319","article-title":"Direct Synthesis of \u03b1-Amino Amides from N-Alkyl Amines by the Copper-Catalyzed Oxidative Ugi-Type Reaction","volume":"23","author":"Ye","year":"2012","journal-title":"Synlett"},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"13121","DOI":"10.1021\/acs.joc.8b01868","article-title":"Iminium Ion and N-hydroxyimide as the Surrogate Components in DEAD-Promoted Oxidative Ugi Variant","volume":"83","author":"Wang","year":"2018","journal-title":"J. Org. Chem."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"4260","DOI":"10.1039\/C5OB00201J","article-title":"Visible Light Mediated sp3 C-H Bond Functionalization of N-Aryl-1,2,3,4-tetrahydroisoquinolines via Ugi-Type Three-Component Reaction","volume":"13","author":"Chen","year":"2015","journal-title":"Org. Biomol. Chem."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"9488","DOI":"10.1021\/acs.joc.2c00382","article-title":"Synthesis of 4-Tetrazolyl-Substituted 3,4-Dihydroquinazoline Derivatives with Anticancer Activity via a One-Pot Sequential Ugi-Azide\/Palladium-Catalyzed Azide-Isocyanide Cross-Coupling\/Cyclization Reaction","volume":"87","author":"Xiong","year":"2022","journal-title":"J. Org. Chem."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"1053","DOI":"10.1055\/s-0037-1611817","article-title":"New Facile Synthesis of 3,4-Dihydroquinazoline-2(1H)-thiones by a Sequential Ugi-Azide\/Staudinger\/Aza-Wittig\/Cyclization Reaction","volume":"30","author":"Xiong","year":"2019","journal-title":"Synlett"},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"1003","DOI":"10.1055\/s-0039-1690831","article-title":"Efficient Synthesis of 4H-3,1-Benzoxazine Derivatives via One-Pot Sequential Passerini-Azide\/Palladium-Catalyzed Azide\u2013Isocyanide Coupling\/Cyclization Reaction","volume":"31","author":"Xiong","year":"2020","journal-title":"Synlett"},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"1072","DOI":"10.1016\/j.tet.2019.01.014","article-title":"One-pot and regioselective synthesis of polysubstituted 3,4-dihydroquinazolines and 4,5-dihydro-3H-1,4-benzodiazepin-3-ones by sequential Ugi\/Staudinger\/aza-Wittig reaction","volume":"75","author":"Xiong","year":"2019","journal-title":"Tetrahedron"},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"5720","DOI":"10.1016\/j.tet.2017.08.011","article-title":"One-pot and regioselective synthesis of 3,4-dihydroquinazolines by Sequential Ugi\/Staudinger\/aza-Wittig reaction starting from functionalized isocyanides","volume":"73","author":"Xiong","year":"2017","journal-title":"Tetrahedron"},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"13125","DOI":"10.1021\/acs.joc.3c01341","article-title":"Synthesis of Imidazo[1,2-a]pyridine-Fused 1,3-Benzodiazepine Derivatives with Anticancer Activity via a One-Pot Cascade GBB-3CR\/Pd(II)-Catalyzed Azide-Isocyanide Coupling\/Cyclization Process","volume":"88","author":"Zhong","year":"2023","journal-title":"J. Org. Chem."},{"key":"ref_49","first-page":"19","article-title":"An Improved Synthesis of N-Isocyanoiminotriphenylphosphorane and Its Use in the Preparation of Diazoketones","volume":"1","author":"Bio","year":"2005","journal-title":"Synthesis"}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/29\/6\/1253\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T14:12:11Z","timestamp":1760105531000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/29\/6\/1253"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2024,3,12]]},"references-count":49,"journal-issue":{"issue":"6","published-online":{"date-parts":[[2024,3]]}},"alternative-id":["molecules29061253"],"URL":"https:\/\/doi.org\/10.3390\/molecules29061253","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2024,3,12]]}}}