Fe(acac)2/TBHP-promoted synthesis of 11-functionalized dibenzodiazepines via alkoxycarbonylation and carboxamidation of o-isocyanodiaryl amines

Sitian Yuan; Yi Liu; Mengjia Ni; Tianxin Hao; Yiyuan Peng; Qiuping Ding

doi:10.1039/D2CC04348C

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Fe(acac)₂/TBHP-promoted synthesis of 11-functionalized dibenzodiazepines via alkoxycarbonylation and carboxamidation of o-isocyanodiaryl amines†

Sitian Yuan,^a Yi Liu,^a Mengjia Ni,^a Tianxin Hao,^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, Jiangxi, China
E-mail: dingqiuping@jxnu.edu.cn

Abstract

A radical addition/cyclization reaction of o-isocyanodiaryl amines has been developed for the efficient synthesis of potentially bioactive dibenzo[b,e][1,4]diazepine-11-carboxylates and dibenzo[b,e][1,4]diazepine-11-carboxamides. This Fe(acac)₂/TBHP-promoted radical cascade process involves an unexplored isocyanide addition and the following cyclization to form 11-functionalized dibenzodiazepines. Moreover, the alkoxycarbonylation and carboxamidation of o-isocyanodiaryl amines show broad substrate scope and good functional group compatibility under mild conditions.

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Article information

DOI: https://doi.org/10.1039/D2CC04348C
Article type: Communication
Submitted: 03 Aug 2022
Accepted: 02 Sep 2022
First published: 05 Sep 2022

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Chem. Commun., 2022,58, 10985-10988

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Fe(acac)₂/TBHP-promoted synthesis of 11-functionalized dibenzodiazepines via alkoxycarbonylation and carboxamidation of o-isocyanodiaryl amines

S. Yuan, Y. Liu, M. Ni, T. Hao, Y. Peng and Q. Ding, Chem. Commun., 2022, 58, 10985 DOI: 10.1039/D2CC04348C

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