Issue 48, 2019

Metal-free switchable ortho/ipso-cyclization of N-aryl alkynamides: divergent synthesis of 3-selenyl quinolin-2-ones and azaspiro[4,5]trienones

Abstract

A selenium radical triggered switchable ortho/ipso-cyclization cascade of N-aryl alkynamides has been devised under metal-free conditions to access 3-selenyl quinolin-2-ones and 3-selenospiro[4,5]trienones in high yields (up to 98%). The simple protocol is scalable and the mechanistic studies suggest that the radical cascade proceeds through a spirocyclic intermediate which is formed via an intramolecular ipso-cyclization route.

Graphical abstract: Metal-free switchable ortho/ipso-cyclization of N-aryl alkynamides: divergent synthesis of 3-selenyl quinolin-2-ones and azaspiro[4,5]trienones

Supplementary files

Article information

Article type
Communication
Submitted
08 Oct 2019
Accepted
19 Nov 2019
First published
20 Nov 2019

Org. Biomol. Chem., 2019,17, 10163-10166

Metal-free switchable ortho/ipso-cyclization of N-aryl alkynamides: divergent synthesis of 3-selenyl quinolin-2-ones and azaspiro[4,5]trienones

H. Sahoo, G. S. Grandhi, I. Ramakrishna and M. Baidya, Org. Biomol. Chem., 2019, 17, 10163 DOI: 10.1039/C9OB02177A

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