5,6,7,8-Tetrahydroquinolines. Part III. Synthesis of 5,6,7,8-tetrahydroquinoline-8-thiocarboxamides

Abstract

Reactions of the 8-lithio-derivative of 5,6,7,8-tetrahydroquinolines with trimethylsilyl isocyanate and isothiocyanate, followed by mild hydrolysis, provide a convenient one-step synthesis of 5,6,7,8-tetrahydroquinoline-8-carboxamides and thio-carboxamides respectively. The corresponding secondary thioamides were prepared by a similar reaction with appropriately substituted isothiocyanates.