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Facile Synthesis of Functionalized 1,4‐Benzodiazepine‐3‐One‐5‐Acetates via [4 + 3]‐Annulation of Azaoxyallyl Cations With 2‐Aminophenyl α,β‐Unsaturated Esters
Author(s) -
Jang Hyun Sun,
Kwon Yong Il,
Kim SungGon
Publication year - 2020
Publication title -
bulletin of the korean chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.237
H-Index - 59
ISSN - 1229-5949
DOI - 10.1002/bkcs.12060
Subject(s) - annulation , chemistry , intramolecular force , yield (engineering) , benzodiazepine , medicinal chemistry , benzazepines , combinatorial chemistry , organic chemistry , stereochemistry , catalysis , receptor , biochemistry , materials science , metallurgy
A metal‐free [4 + 3]‐annulation of α‐halohydroxamates with 2‐aminophenyl α,β‐unsaturated esters has been developed for the construction of seven‐membered 1,4‐benzodiazepine‐3‐one‐5‐acetates in moderate to good yields (up to 82% yield). The annulation involved the cascade reaction of an generation of azaoxyallyl cation, aza‐addition to this azaoxyallyl cation, and intramolecular aza‐Michael reaction to yield 1,4‐benzodiazepine‐3‐one‐5‐acetates.