Premium
A one‐pot procedure for ring enlargement of α‐chloromethyl N ‐containing heterocycles
Author(s) -
Zheng Lianyou,
Xiang Jinbao,
Bai Xu
Publication year - 2006
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570430211
Subject(s) - chemistry , ring (chemistry) , bromide , medicinal chemistry , benzyl bromide , salt (chemistry) , tetrahydroisoquinoline , stereochemistry , organic chemistry , catalysis
A simple one‐pot procedure for ring enlargement of α‐chloromethyl N ‐containing heterocycles has been developed. By reaction of chloromethyl tetrahydroisoquinoline and its thieno analog with benzyl or allyl bromide under basic conditions, ring expansion and N ‐substitution were achieved simultaneously. The key to the transformation was proposed to involve the formation of aziridinium salt and subsequent bond breaking between the nitrogen and tertiary carbon atoms.