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

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 involv...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2022-09, Vol.58 (78), p.10985-10988
Main Authors: Yuan, Sitian, Liu, Yi, Ni, Mengjia, Hao, Tianxin, Peng, Yiyuan, Ding, Qiuping
Format: Article
Language:English
Subjects:
Amines
Biocompatibility
Carboxylates
Functional groups
Substrates
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Summary: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.
ISSN:1359-7345
1364-548X
DOI:10.1039/d2cc04348c