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

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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

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Publication details

The article was received on 08 Oct 2019, accepted on 19 Nov 2019 and first published on 20 Nov 2019


Article type: Communication
DOI: 10.1039/C9OB02177A
Org. Biomol. Chem., 2019, Advance Article

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    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, Advance Article , DOI: 10.1039/C9OB02177A

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