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Zinc (II)-Mediated Selective O-Benzylation of 2-Oxo-1,2-Dihydropyridines Systems.


ABSTRACT: The selective O-benzylation of 2-oxo-1,2-dihydropyridines plays a critical role in organic synthesis of natural products and biological active molecules. Herein we report a novel ternary system of ZnO, ZnCl? and N,N-diisopropylethylamine (DIEA), that is highly effective for selective O-benzylation of 2-oxo-1,2-dihydropyridines using abundant substituted benzyl halides and related substituted 2-oxo-1,2-dihydropyridines compounds. This process allows access to a variety of O-benzyl products under mild reaction conditions, which are important synthetic intermediates in the protection of functional groups, and represents a new method toward the development for the O-benzylation of 2-oxo-1,2-dihydropyridines.

SUBMITTER: Zhou Q 

PROVIDER: S-EPMC6100589 | biostudies-literature | 2018 Jul

REPOSITORIES: biostudies-literature

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Zinc (II)-Mediated Selective <i>O</i>-Benzylation of 2-Oxo-1,2-Dihydropyridines Systems.

Zhou Qifan Q   Du Fangyu F   Liang Xinjie X   Liu Wenqiang W   Fang Ting T   Chen Guoliang G  

Molecules (Basel, Switzerland) 20180720 7


The selective <i>O</i>-benzylation of 2-oxo-1,2-dihydropyridines plays a critical role in organic synthesis of natural products and biological active molecules. Herein we report a novel ternary system of ZnO, ZnCl₂ and <i>N</i>,<i>N</i>-diisopropylethylamine (DIEA), that is highly effective for selective <i>O</i>-benzylation of 2-oxo-1,2-dihydropyridines using abundant substituted benzyl halides and related substituted 2-oxo-1,2-dihydropyridines compounds. This process allows access to a variety  ...[more]

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