Reactions of Heterocumulenes with Organometallic Reagents:VIII.~* Reactions of Carbanions Derived from Alkoxy-and Alkylsulfanylethenes with Isothiocyanates-A Convenient Route to 2-Propenethioamides,1-Methylsulfanyl-2-propen-l-imines,and Benzothiazole

摘要

Metalated alkoxy- and alkylsulfanylethenes readily add to isothiocyanates;the subsequent hydrolysis or alkylation of the adducts leads to formation of 2-propenethioamides or 1-methylsulfanyl-2- propen-1-imines(as mixtures of syn and anti isomers)in 74-100% yield.The reaction of metalated alkoxyethenes with 2-fluorophenyl isothiocyanate opens the way to new benzothiazole derivatives.Hydrolysis of the latter provides a simple method for the preparation of 2-benzothiazolyl ketones.