Synthesis, Table of Contents Synthesis 2021; 53(23): 4419-4427DOI: 10.1055/a-1543-3924 feature Visible-Light Photocatalytic Ugi/Aza-Wittig Cascade towards 2-Aminomethyl-1,3,4-oxadiazole Derivatives Camilla Russo a Department of Pharmacy, University of Naples Federico II, via D. Montesano 49, 80131, Napoli, Italy , Rolando Cannalire a Department of Pharmacy, University of Naples Federico II, via D. Montesano 49, 80131, Napoli, Italy , Paolo Luciano a Department of Pharmacy, University of Naples Federico II, via D. Montesano 49, 80131, Napoli, Italy , Francesca Brunelli b Department of Drug Science, University of Piemonte Orientale, Largo Donegani 2, 28100, Novara, Italy , Gian Cesare Tron b Department of Drug Science, University of Piemonte Orientale, Largo Donegani 2, 28100, Novara, Italy , Mariateresa Giustiniano∗ a Department of Pharmacy, University of Naples Federico II, via D. Montesano 49, 80131, Napoli, Italy› Author AffiliationsRecommend Article Abstract Buy Article All articles of this category Abstract A new visible-light photocatalytic multicomponent reaction (MCR) involving N-alkyl-N-methylanilines, N-isocyanoiminotriphenylphosphorane, and carboxylic acids leading to 1,3,4-oxadiazole derivatives is reported. The developed mild reaction conditions enable a broad substrate scope and good functional group tolerance, as further highlighted in the late-stage functionalization of amino acids and drugs. Additionally, a two-step one-pot protocol for the synthesis of non-symmetrical diacylhydrazines is also reported. Key words Key wordsphotoredox catalysis - isocyanide chemistry - Ugi reaction - aza-Wittig reaction - multicomponent reactions - 1,3,4-oxadiazoles Full Text References References 1 Boström J, Hogner A, Llinàs A, Wellner E, Plowright AT. J. Med. Chem. 2012; 55: 1817 2 Li Z, Zhan P, Liu X. Mini-Rev. Med. Chem. 2011; 11: 1130 3 Goldberg K, Groombridge S, Hudson J, Leach AG, MacFaul PA, Pickup A, Poultney R, Scott JS, Svensson PH, Sweeney J. MedChemComm 2012; 3: 600 4 Frost JR, Scully CC. G, Yudin AK. Nat. Chem. 2016; 8: 1105 5 Dömling A, Ugi I. Angew. Chem. Int. Ed. 2000; 39: 3168 6 Dömling A, Wang W, Wang K. Chem. Rev. 2012; 112: 3083 7 Ramazani A, Rezaei A. Org. Lett. 2010; 12: 2852 8 Vachhani DD, Sharma A, Van der Eycken E. Angew. Chem. Int. Ed. 2013; 52: 2547 9 Wang Q, Mgimpatsang KC, Konstantinidou M, Shishkina SV, Dömling A. Org. Lett. 2019; 21: 7320 10 Sun M, Zhao L, Yu YL, Ding MW. Synthesis 2021; 53: 1365 11 Stephenson C, Yoon T, MacMillan DW. C. Visible Light Photocatalysis in Organic Chemistry . Wiley-VCH; Weinheim: 2018 12 Douglas JJ, Sevrin MJ, Stephenson CR. J. Org. Process Res. Dev. 2016; 20: 1134 13 Garbarino S, Ravelli D, Protti S, Basso A. Angew. Chem. Int. Ed. 2016; 55: 15476 14 Rueping M, Vila C. Org. Lett. 2013; 15: 2092 15 Vila C. Rueping M. 2013; 15: 2056 16 Rueping M, Vila C, Bootwicha T. ACS Catal. 2013; 3: 1676 17 Souldozi A, Ramazani A. Tetrahedron Lett. 2007; 48: 1549 18 Reckenthäler M, Griesbeck AG. Adv. Synth. Catal. 2013; 355: 2727 19 Cannalire R, Pelliccia S, Sancineto L, Novellino E, Tron GC, Giustiniano M. Chem. Soc. Rev. 2021; 50: 766 20 Zarei M, Nakhli ME. Res. Chem. Intermed. 2017; 43: 1909 21 Zareef M, Iqbal R, Mirza B, Khan KM, Manan A, Asim F, Khan SW. Arkivoc 2008; (ii): 141 22 Cui Z.-N, Huang J, Li Y, Ling Y, Yang X.-L, Chen F.-H. Chin. J. Chem. 2008; 26: 916 23 Komaraiah A, Sailu B, Reddy PS. N. Synth. Commun. 2008; 38: 114 24 Roth HG, Romero NA, Nicewicz DA. Synlett 2016; 27: 714 25 Crisenza GE. M, Melchiorre P. Nat. Commun. 2020; 11: 803 Supplementary Material Supplementary Material Supporting Information
