Divergent Synthesis of Chalcogenylated Quinolin-2-ones and Spiro[4,5]trienones via Intramolecular Cyclization of N-Aryl­propynamides Mediated by Diselenides/Disulfides and PhICl₂

Abstract

The reaction of N-arylpropynamides with (dichloroiodo)benzene (PhICl₂) and diselenides/disulfides resulted in a divergent synthesis of chalcogenylated quinolinones and spiro[4.5]trienes through intramolecular electrophilic cyclization and chalcogenylation. The chalcogenyl functional group was introduced by an electrophilic reactive organosulfenyl chloride or selenenyl chloride species, generated in situ from the reaction of disulfides/diselenides and PhICl₂. Notably, the divergent cyclization pathways were determined by the substituent type on the aniline ring in N-arylpropynamide substrates. Substrates bearing a fluoro, methoxy or trifluoromethoxy group at the para-position of the aniline underwent an alternative spiralization pathway to give the 3-chalcogenylated spiro[4,5]trienones.

Key words

quinolin-2-ones - diselenides/disulfides - PhICl₂ - intramolecular cyclization - spiro[4,5]trienones

Publication History

Received: 18 September 2021

Accepted after revision: 17 October 2021

Article published online:
29 November 2021

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