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  • Me3SiCl-promoted three-component coupling reaction of a functionalized enamine, an acetal, and an alkyne: an unprecedented approach to the synthesis of tetrasubstituted pyridines via a [3 + 2 + 1] intermolecular cyclization.

Me3SiCl-promoted three-component coupling reaction of a functionalized enamine, an acetal, and an alkyne: an unprecedented approach to the synthesis of tetrasubstituted pyridines via a [3 + 2 + 1] intermolecular cyclization.

The Journal of organic chemistry (2008-07-30)
Toshiaki Sasada, Norio Sakai, Takeo Konakahara
ABSTRACT

We have identified a Me3SiCl-mediated three-component coupling reaction of a functionalized enamine, N,N-dimethylformamide diethyl acetal, and an internal alkyne having an electron-withdrawing group that produces 2,3,4,5-tetrasubstituted pyridine derivatives in good to excellent yields via a single-step reaction.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
N,N-Dimethylformamide diethyl acetal, 95%
Sigma-Aldrich
N,N-Dimethylformamide diethyl acetal, for esterification of fatty acids, ≥95.0% (GC)
Sigma-Aldrich
N,N-Dimethylformamide dimethyl acetal, technical grade, 94%