Issue 30, 2022

Silver-promoted dearomative [3+4] cycloaddition of anthranils with α-isocyanoacetates: access to benzodiazepines

Abstract

The first example of silver-promoted [3+4] cycloaddition of α-isocyanoacetates with anthranils as aromatic Michael accepters, offering access to benzo[d][1,3]diazepinones, has been developed. Mechanistic studies revealed that an “oxygen migration” rearrangement process was involved in this dearomative cycloaddition reaction. Additionally, benzo[d][1,3]diazepinones were obtained efficiently as well under catalytic conditions. Broad functional groups were well tolerated under mild reaction conditions.

Graphical abstract: Silver-promoted dearomative [3+4] cycloaddition of anthranils with α-isocyanoacetates: access to benzodiazepines

Supplementary files

Article information

Article type
Communication
Submitted
09 Feb 2022
Accepted
17 Mar 2022
First published
18 Mar 2022

Chem. Commun., 2022,58, 4771-4774

Silver-promoted dearomative [3+4] cycloaddition of anthranils with α-isocyanoacetates: access to benzodiazepines

R. Shao, H. Zhao, S. Ding, L. Li, C. Chen, J. Wang and Y. Shang, Chem. Commun., 2022, 58, 4771 DOI: 10.1039/D2CC00807F

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