Subscribe to RSS
DOI: 10.1055/a-1543-3924
Visible-Light Photocatalytic Ugi/Aza-Wittig Cascade towards 2-Aminomethyl-1,3,4-oxadiazole Derivatives
Financial support from Università degli Studi di Napoli Federico II and Università del Piemonte Orientale, Novara, Italy is acknowledged. M. G. acknowledges PROGEMA support (ARS01_X00432, PON R&I 2014-2020). R. C. acknowledges support from Ministero dell’Istruzione, dell’Università e della Ricerca (MIUR; Italian Ministry of Education, University and Research), PON R&I 2014-2020-AIM (Attraction and International Mobility), project AIM1873131 - Num. Attività 2 - Linea 2.1.
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
photoredox catalysis - isocyanide chemistry - Ugi reaction - aza-Wittig reaction - multicomponent reactions - 1,3,4-oxadiazolesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1543-3924.
- Supporting Information
Publication History
Received: 14 May 2021
Accepted after revision: 02 July 2021
Accepted Manuscript online:
02 July 2021
Article published online:
13 August 2021
© 2021. Thieme. All rights reserved
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany
-
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