Issue 8, 2017

Silver(i) catalyzed intramolecular cyclization of N-(2-(alk-1-yn-1-yl))-1H-tetrazoles leading to the formation of N-cyano-2-substituted indoles under ambient conditions

Abstract

A facile silver(I) catalyzed intramolecular cyclization reaction of alkynyl tetrazoles to form N-cyano-2-substituted indoles has been investigated. This unique cyclization involves the formation of a C–N bond during the intramolecular cyclization of N-(2-(alk-1-yn-1-yl))-1H-tetrazoles in the presence of silver(I) acetate. Good to excellent yields were obtained using low catalyst loadings, ∼5 mol%, under mild conditions.

Graphical abstract: Silver(i) catalyzed intramolecular cyclization of N-(2-(alk-1-yn-1-yl))-1H-tetrazoles leading to the formation of N-cyano-2-substituted indoles under ambient conditions

Supplementary files

Article information

Article type
Research Article
Submitted
08 Feb 2017
Accepted
03 May 2017
First published
05 May 2017

Org. Chem. Front., 2017,4, 1574-1579

Silver(I) catalyzed intramolecular cyclization of N-(2-(alk-1-yn-1-yl))-1H-tetrazoles leading to the formation of N-cyano-2-substituted indoles under ambient conditions

S. Panaka, R. Trivedi, T. Sony, S. Prabhakar and L. Raju Chowhan, Org. Chem. Front., 2017, 4, 1574 DOI: 10.1039/C7QO00109F

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