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A one-pot procedure for ring enlargement of α-chloromethyl N-containing heterocycles

✍ Scribed by Lianyou Zheng; Jinbao Xiang; Xu Bai


Publisher
Journal of Heterocyclic Chemistry
Year
2006
Tongue
English
Weight
254 KB
Volume
43
Category
Article
ISSN
0022-152X

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✦ Synopsis


A simple one-pot procedure for ring enlargement of -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.


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