Issue 22, 2017

Intramolecular cascade rearrangements of enynamine derived ketenimines: access to acyclic and cyclic amidines

Abstract

Copper-catalyzed reaction of enynamines with sulfonylazides provides acyclic and cyclic amidines. Nucleophilic addition of the tethered amino group on the in situ generated ketenimine forms a six-membered cyclic zwitterionic intermediate which facilitates migration of the tethered amino group to the C5-center giving the acyclic amidine. On the other hand, migration of a substituent on the amino group to C2- and C4-centers results in the formation of cyclic amidines. Computational studies were carried out to validate the mechanism which indicates that the product distribution of the process depends on the substitutions on the enynamine backbone.

Graphical abstract: Intramolecular cascade rearrangements of enynamine derived ketenimines: access to acyclic and cyclic amidines

Supplementary files

Article information

Article type
Paper
Submitted
28 Feb 2017
Accepted
09 May 2017
First published
09 May 2017

Org. Biomol. Chem., 2017,15, 4822-4830

Intramolecular cascade rearrangements of enynamine derived ketenimines: access to acyclic and cyclic amidines

D. P. Chauhan, S. J. Varma, M. Gudem, N. Panigrahi, K. Singh, A. Hazra and P. Talukdar, Org. Biomol. Chem., 2017, 15, 4822 DOI: 10.1039/C7OB00499K

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