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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