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‘Atypical Ugi’ tetrazoles

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Abstract

Amino acid-derived isocyano amides together with TMSN3, oxocomponents and 1° or 2° amines are common substrates in the Ugi tetrazole reaction. We surprisingly found that combining these substrates gives two different constitutional isomeric Ugi products A and B. A is the expected classical Ugi product whereas B is an isomeric product (‘atypical Ugi’) of the same molecular weight with the tetrazole heterocycle migrated to a different position. We synthesized, separated and characterized 22 different isomorphic examples of the two constitutional isomers of the Ugi reaction to unambiguously prove the formation of A and B. Mechanistic studies resulted in a proposed mechanism for the concomitant formation of A and B.

Graphical abstract: ‘Atypical Ugi’ tetrazoles

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Article information


Submitted
26 Nov 2019
Accepted
07 Jan 2020
First published
07 Jan 2020

This article is Open Access

Chem. Commun., 2020, Advance Article
Article type
Communication

‘Atypical Ugi’ tetrazoles

E. M. M. Abdelraheem, I. Goodwin, S. Shaabani, M. P. de Haan, K. Kurpiewska, J. Kalinowska-Tłuścik and A. Dömling, Chem. Commun., 2020, Advance Article , DOI: 10.1039/C9CC09194G

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