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One‐Pot Synthesis of 2‐Substituted 4‐Aryl‐4,5‐dihydro‐3,1‐benzoxazepines from 2‐(2‐Aminophenyl)‐1‐arylethanols via Dehydration of the Corresponding Amides
Author(s) -
Fukamachi Shuhei,
Konishi Hisatoshi,
Kobayashi Kazuhiro
Publication year - 2011
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201000421
Subject(s) - chemistry , dehydration , aryl , dehydration reaction , medicinal chemistry , organic chemistry , biochemistry , alkyl
An efficient method for the preparation of 2‐substituted 4‐aryl‐4,5‐dihydro‐3,1‐benzoxazepine derivatives under mild conditions has been developed. The reaction of 2‐(2‐aminophenyl)ethanols 1 with acid chlorides in the presence of excess Et 3 N in THF at room temperature gave the corresponding N ‐acylated intermediates 2 , which were dehydrated by treatment with POCl 3 to give 2‐substituted 4‐aryl‐4,5‐dihydro‐3,1‐benzoxazepines 3 in a one‐pot reaction.