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

Toshiaki Sasada; Norio Sakai; Takeo Konakahara

doi:10.1021/jo801090h

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

J Org Chem. 2008 Sep 5;73(17):6905-8. doi: 10.1021/jo801090h. Epub 2008 Jul 29.

Authors

Toshiaki Sasada¹, Norio Sakai, Takeo Konakahara

Affiliation

¹ Department of Pure and Applied Chemistry, Faculty of Science and Technology, Tokyo University of Science (RIKADAI), Noda, Chiba 278-8510, Japan.

PMID: 18661946
DOI: 10.1021/jo801090h

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Acetals / chemistry*
Alkynes / chemistry*
Amines / chemistry*
Crystallography, X-Ray
Cyclization
Dimethylformamide
Formamides / chemistry*
Models, Chemical
Pyridines / chemical synthesis*
Trimethylsilyl Compounds / chemistry*

Substances

Acetals
Alkynes
Amines
Formamides
Pyridines
Trimethylsilyl Compounds
Dimethylformamide