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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

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-... Full description

Journal Title: The Journal of organic chemistry 05 September 2008, Vol.73(17), pp.6905-8
Main Author: Sasada, Toshiaki
Other Authors: Sakai, Norio , Konakahara, Takeo
Format: Electronic Article Electronic Article
Language: English
Subjects:
ID: E-ISSN: 1520-6904 ; PMID: 18661946 Version:1 ; DOI: 10.1021/jo801090h
Link: http://pubmed.gov/18661946
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recordid: medline18661946
title: 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
format: Article
creator:
  • Sasada, Toshiaki
  • Sakai, Norio
  • Konakahara, Takeo
subjects:
  • Acetals -- Chemistry
  • Alkynes -- Chemistry
  • Amines -- Chemistry
  • Formamides -- Chemistry
  • Pyridines -- Chemical Synthesis
  • Trimethylsilyl Compounds -- Chemistry
ispartof: The Journal of organic chemistry, 05 September 2008, Vol.73(17), pp.6905-8
description: 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.
language: eng
source:
identifier: E-ISSN: 1520-6904 ; PMID: 18661946 Version:1 ; DOI: 10.1021/jo801090h
fulltext: fulltext
issn:
  • 15206904
  • 1520-6904
url: Link


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subjectAcetals -- Chemistry ; Alkynes -- Chemistry ; Amines -- Chemistry ; Formamides -- Chemistry ; Pyridines -- Chemical Synthesis ; Trimethylsilyl Compounds -- Chemistry
descriptionWe 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.
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descriptionWe 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.
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titleMe3SiCl-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
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atitleMe3SiCl-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
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abstractWe 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.
doi10.1021/jo801090h
pmid18661946
date2008-09-05