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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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
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container_end_page 487
container_issue 3
container_start_page 483
container_title Synlett
container_volume 2010
creator Yang, Hao
Li, Zhu-Bo
Shin, Dong-Soo
Wang, Li-Ying
Zhou, Jia-Zhou
Qiao, Hong-Bo
Tian, Xiao
Ma, Xiao-Yan
Zuo, Hua
description 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.
doi_str_mv 10.1055/s-0029-1219190
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title A Facile C-N Bond Formation: One-Pot Reaction of Phenols and Amines via Smiles Rearrangement
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