A Facile C-N Bond Formation: One-Pot Reaction of Phenols and Amines via Smiles Rearrangement

Abstract Diarylamines and arylalkylamines were synthesized in high yields from 2-chlorophenols and amines, activated by chloroacetyl chloride under microwave irradiation (20-60 min) or conventional thermal conditions (3-6 h). The key transformation is believed to proceed via Smiles rearrangement by...

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Bibliographic Details
Published in:Synlett 2010-02, Vol.2010 (3), p.483-487
Main Authors: Yang, Hao, Li, Zhu-Bo, Shin, Dong-Soo, Wang, Li-Ying, Zhou, Jia-Zhou, Qiao, Hong-Bo, Tian, Xiao, Ma, Xiao-Yan, Zuo, Hua
Format: Article
Language:English
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Summary:Abstract Diarylamines and arylalkylamines were synthesized in high yields from 2-chlorophenols and amines, activated by chloroacetyl chloride under microwave irradiation (20-60 min) or conventional thermal conditions (3-6 h). The key transformation is believed to proceed via Smiles rearrangement by initial O-alkylation and subsequent cyclization.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0029-1219190