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Divergent Synthesis of α,α‐Dihaloamides through α,α‐Dihalogenation of β‐Oxo Amides by Using N ‐Halosuccinimides
Author(s) -
Wang Jia,
Li Hongtao,
Zhang Dingyuan,
Huang Peng,
Wang Zikun,
Zhang Rui,
Liang Yongjiu,
Dong Dewen
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201300341
Subject(s) - chemistry , ethanol , organic chemistry , reaction conditions , medicinal chemistry , stereochemistry , catalysis
An efficient and divergent one‐pot synthesis of α,α‐dihaloamides from readily available β‐oxo amides based on the selection of reaction conditions is reported. α,α‐Dihalo‐β‐oxo amides were produced by treating β‐oxo amides with N ‐chlorosuccinimide (NCS) or N ‐bromosuccinimide (NBS) in water at room temperature, whereas α,α‐dihaloacetamides were synthesized by subjecting β‐oxo amides to NCS or NBS in ethanol under reflux.