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 alpha- and beta-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.
Matsuya
Yuji
Y
Graduate School of Medicine and Pharmaceutical Sciences, University of Toyama, 2630 Sugitani, Toyama 930-0194, Japan.
Hayashi
Kousuke
K
Wada
Akiho
A
Nemoto
Hideo
H
D000480:Alkynes / Q000737:chemistry*; D003500:Cyclization; D007097:Imines / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D010879:Piperazines / Q000737:chemistry*; D011422:Propionates / Q000737:chemistry*; D013055:Spectrophotometry, Infrared; D014297:Trimethylsilyl Compounds / Q000737:chemistry*
D000480:Alkynes; D007097:Imines; D010879:Piperazines; D011422:Propionates; D014297:Trimethylsilyl Compounds; C011537:propiolic acid; C007306:triethylenediamine