Three-component bis-heterocycliation for synthesis of 2-aminobenzo[4,5]thieno[3,2-d]thiazoles

Literature Information

Publication Date 2019-02-26
DOI 10.1039/C8QO01365A
Impact Factor 5.281
Authors

Huawen Huang, Zhonghua Qu, Xiaochen Ji, Guo-Jun Deng


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Abstract

A cooperative base system has been developed for the novel three component bis-heterocyclization of methylketoxime acetates. In a reaction complementary to previous thiazole and benzo[4,5]thieno[3,2-d]thiazole formation, the present protocol provides an effective entry to 2-aminobenzo[4,5]thieno[3,2-d]thiazoles. Mechanistically, the formation of trisulfur radical anion [S3]˙− and Willgerodt–Kindler-type sulfuration would be the key for this transformation.

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