C. D. Tollenaere, L. Ghosez
Sep 1, 1998
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Journal
Bulletin de la Société Chimique de France
Abstract
1-[(tert-Butyldimethylsilyl)oxy] alkenyl isocyanates 1a and 1b have been conveniently prepared from acetyl or propionyl chloride, silver cyanate and tert-butyldimethylsilyl triflate in the presence of triethylamine. They react with electron-deficient acetylenic dienophiles or with tosyl cyanide to give highly functionalised pyridines or derivatives of uracil or thymine in moderate yields. They also cycloadd with 1-(diethylamino)prop-1-yne, an electron-rich dienophile, to yield glutaconimides and pyridine derivatives.