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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| Authors: | Nedolya N A Shlyakhtina N I Sarapulova G I Brandsma L |
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| Institution: | (1) Favorskii Irkutsk Institute of Chemistry, Siberian Division, Russian Academy of Sciences, ul. Favorskogo 1, Irkutsk, 664033, Russia;(2) Utrecht University, Utrecht, The Netherlands |
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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 synand antiisomers) 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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