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-1-imines, and Benzothiazoles


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Abstract

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.

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