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Synthesis of new5-alkylidene-4-chloro-5H-1,2,3-dithiazoles and their stereochemistry

✍ Scribed by Moon-Kook Jeon; Kyongtae Kim

Publisher: Elsevier Science
Year: 1999
Tongue: French
Weight: 948 KB
Volume: 55
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(99)00585-2

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✦ Synopsis

A variety of 5-alkylidene-4-chloro-5H-I,2,3-dithiazoles (9-25) have been prepared from 4chloro-5H-l,2,3-dithiazolium chloride, active methylene compounds, and pyridine. The reactions with ethyl nitroacetate ((Z) > (E)), ethyl 3-nitrobenzoylacetate ((E) > (Z)), ethyl 2-fluorobenzoylacetate ((E) > (Z)), and tetronic acid ((Z) > (E)) gave a mixture of(E)-and (Z)-isomers, whereas those of benzoylnitromethane (Z), 5,6-dihydro-4-hydroxy-6-methyl-2H-pyran-2-one (E), 4-hydroxy-6-methyl-2-pyrone (E), 4-hydroxycoumarin (E), 6-chloro-4-hydroxycoumarin (E), and 6-bromo--4-hydroxycoumarin (E) afforded only single stereoisomers. The reactions with 4-hydroxy-l-methyl-2(1/-/)-quinolone, 2-hydroxy-l,4-naphthoquinone and homophthalic anhydride gave only single stereoisomers whose stereochemistry is uncertain. It appears that geometrically more rigid cyclic 1,3-dicarbonyl compounds give better yields of dithiazol-5-ylidenes than the corresponding acyclic compounds.

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