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Synthesis of 1,4‐Benzoxazepine Derivatives via a Novel Domino Aziridine Ring‐Opening and Isocyanide‐Insertion Reaction
Author(s) -
Ji Fei,
Lv Meifang,
Yi Wenbin,
Cai Chun
Publication year - 2013
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201300650
Subject(s) - isocyanide , aziridine , chemistry , regioselectivity , domino , ring (chemistry) , cascade reaction , combinatorial chemistry , palladium , insertion reaction , stereochemistry , organic chemistry , catalysis
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.