One-pot synthesis of 11-sulfenyl dibenzodiazepines via tandem sulfenylation/cyclization of o-isocyanodiaryl amines and diaryl disulfides

Yi Liu; Wei Gao; Sitian Yuan; Mengjia Ni; Tianxin Hao; Cuiying Zeng; Xinyi Xu; Yang Fu; Yiyuan Peng; Qiuping Ding

doi:10.1039/D3OB00220A

One-pot synthesis of 11-sulfenyl dibenzodiazepines via tandem sulfenylation/cyclization of o-isocyanodiaryl amines and diaryl disulfides†

Yi Liu,^a Wei Gao,*^b Sitian Yuan,^a Mengjia Ni,^a Tianxin Hao,^a Cuiying Zeng,^a Xinyi Xu,^a Yang Fu,

*^a Yiyuan Peng

^a and Qiuping Ding

*^a

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* Corresponding authors

^a National Engineering Research Center for Carbohydrate Synthesis, Key Lab of Fluorine and Silicon for Energy Materials and Chemistry of Ministry of Education, Key Laboratory for Green Chemistry of Jiangxi Province, Jiangxi Normal University, Nanchang 330022, Jiangxi, China
E-mail: yangfu@jxnu.edu.cn, dingqiuping@jxnu.edu.cn

^b Jiangxi Academy of Forestry, Nanchang 330013, Jiangxi, China
E-mail: 284256805@qq.com

Abstract

A one-pot sulfenylation/cyclization of o-isocyanodiaryl amines has been described for the preparation of 11-sulfenyl dibenzodiazepines. This AgI-catalyzed reaction covers an unexplored tandem process to give seven-membered N-heterocycles. This transformation shows a broad range of substrate scope, simple operation, and moderate to good yields under aerobic conditions. Diphenyl diselenide can also be produced in an acceptable yield.

Organic & Biomolecular Chemistry

One-pot synthesis of 11-sulfenyl dibenzodiazepines via tandem sulfenylation/cyclization of o-isocyanodiaryl amines and diaryl disulfides†

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One-pot synthesis of 11-sulfenyl dibenzodiazepines via tandem sulfenylation/cyclization of o-isocyanodiaryl amines and diaryl disulfides

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