Three-Component Coupling Reaction and Cyclization of N-Tosylimines and TMS-Substituted Propiolate Mediated by DABCO

A new three-component coupling reaction of methyl 3-trimethylsilylpropiolate, N-tosylimine, and tosylamide mediated by DABCO was developed. This reaction was based on the consecutive α- and β-activation method of propiolate involving intramolecular silyl migration previously developed by our group....

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Bibliographic Details
Published in:Journal of organic chemistry 2008-03, Vol.73 (5), p.1987-1990
Main Authors: Matsuya, Yuji, Hayashi, Kousuke, Wada, Akiho, Nemoto, Hideo
Format: Article
Language:English
Subjects:
Alkynes - chemistry
Chemistry
Cyclization
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Imines - chemistry
Magnetic Resonance Spectroscopy
Mass Spectrometry
Organic chemistry
Piperazines - chemistry
Preparations and properties
Propionates - chemistry
Spectrophotometry, Infrared
Trimethylsilyl Compounds - chemistry
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Summary:A new three-component coupling reaction of methyl 3-trimethylsilylpropiolate, N-tosylimine, and tosylamide mediated by DABCO was developed. This reaction was based on the consecutive α- and β-activation method of propiolate involving intramolecular silyl migration previously developed by our group. On the basis of these results, a new cyclization reaction was designed to find a chromene-forming reaction utilizing salicyl N-tosylimine as a bifunctional substrate.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo702649q