Synthesis of 1,4-Benzoxazepine Derivatives via a Novel Domino Aziridine Ring-Opening and Isocyanide-Insertion Reaction

A novel and efficient domino process has been developed for the synthesis of 1,4‐benzoxazepine derivatives from a range of readily accessible N‐tosylaziridines, 2‐iodophenols and isocyanides. This process involves the aziridine ring‐opening reaction with 2‐iodophenol, followed by a palladium‐catalyz...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2013-11, Vol.355 (17), p.3401-3406
Main Authors: Ji, Fei, Lv, Mei-fang, Yi, Wen-bin, Cai, Chun
Format: Article
Language:English
Subjects:
1,4‐benzoxazepines
4-benzoxazepines
Accessibility
aziridine ring-opening
Catalysis
Derivatives
domino process
isocyanide-insertion
Natural products
regioselectivity
Synthesis
Transformations
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Summary:A novel and efficient domino process has been developed for the synthesis of 1,4‐benzoxazepine derivatives from a range of readily accessible N‐tosylaziridines, 2‐iodophenols and isocyanides. This process involves the aziridine ring‐opening reaction with 2‐iodophenol, followed by a palladium‐catalyzed isocyanide‐insertion reaction. This regioselective and high‐yielding transformation could be extended to its application for the synthesis of natural products and biologically interesting heterocycles.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201300650