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Metal-free oxidative [2+2+1] heteroannulation of 1,7-enynes with thiocyanates toward thieno[3,4-c]quinolin-4(5H)-ones

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Abstract

A new metal-free oxidative [2+2+1] heteroannulation of 1,7-enynes with thiocyanates for producing thieno[3,4-c]quinolin-4(5H)-ones is presented. This reaction employs benzoylperoxide (BPO) as the oxidant and sodium thiocyanate as the sulfur source to enable the formation of three chemical bonds, two C–S bonds and one C–C bond, in a single reaction, and represents a new, practical access to S-heterocycles with the avoidance of the use of metal catalysts and excess bases.

Graphical abstract: Metal-free oxidative [2+2+1] heteroannulation of 1,7-enynes with thiocyanates toward thieno[3,4-c]quinolin-4(5H)-ones

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Publication details

The article was received on 21 Mar 2019, accepted on 09 May 2019 and first published on 10 May 2019


Article type: Communication
DOI: 10.1039/C9CC02242B
Chem. Commun., 2019, Advance Article

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    Metal-free oxidative [2+2+1] heteroannulation of 1,7-enynes with thiocyanates toward thieno[3,4-c]quinolin-4(5H)-ones

    J. Yu, S. Niu, M. Hu, J. Xiang and J. Li, Chem. Commun., 2019, Advance Article , DOI: 10.1039/C9CC02242B

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