Premium
N,N,N′,N′ ‐Tetramethylchloroformamidinium Chloride‐Mediated Cyclizations of β‐Oxo Amides: Facile and Divergent One‐Pot Synthesis of Substituted 2 H ‐Pyrans, 4 H ‐Pyrans and Pyridin‐2(1 H )‐ones
Author(s) -
Wang Yan,
Xin Xin,
Liang Yongjiu,
Lin Yingjie,
Duan Haifeng,
Dong Dewen
Publication year - 2009
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200900310
Subject(s) - chemistry , triethylamine , one pot synthesis , ethanol , chloride , medicinal chemistry , intermolecular force , sodium hydroxide , organic chemistry , catalysis , molecule
An efficient and divergent one‐pot synthesis of substituted 2 H ‐pyrans, 4 H ‐pyrans and pyridin‐2(1 H )‐ones from β‐oxo amides based on the selection of the reaction conditions is reported. Mediated by N,N,N′,N′ ‐tetramethylchloroformamidinium chloride, β‐oxo amides underwent intermolecular cyclizations in the presence of triethylamine at room temperature to give substituted 2 H ‐pyrans in high yields, which could be converted into substituted 4 H ‐pyrans in the presence of sodium hydroxide in ethanol at room temperature, or into substituted pyridin‐2(1 H )‐ones under reflux.