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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. 2019

Jiang-Xi Yu, and Shijie Niu, and Ming Hu, and Jian-Nan Xiang, and Jin-Heng Li
State Key Laboratory of Chemo/Biosensing and Chemometrics, Hunan University, Changsha 410082, China. jhli@hnu.edu.cn.

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.

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