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The Behavior of (cyclic-alkylidene)hydrazinecarbothioamides in Cyclization with Dimethyl acetylenedicarboxylate

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A series of (Z)-methyl 2(Z)-3-substituted-2-(cycloalkylidenehydrazono)-4-oxothiazolidin-5-ylidene)-acetate derivatives were synthesized via condensation alkylidene-N-substituted hydrazinecarbothioamides with dimethyl acetylenedicarboxylate. The synthesized compounds were characterized by using different spectroscopic methods and confirmed by single crystal… Click to show full abstract

A series of (Z)-methyl 2(Z)-3-substituted-2-(cycloalkylidenehydrazono)-4-oxothiazolidin-5-ylidene)-acetate derivatives were synthesized via condensation alkylidene-N-substituted hydrazinecarbothioamides with dimethyl acetylenedicarboxylate. The synthesized compounds were characterized by using different spectroscopic methods and confirmed by single crystal X-ray analysis. The behavior of (cyclic-alkylidene) hydrazinecarbothioamides in cyclization was presented. The mechanism of transformation of (Z)-methyl 2-((Z)-3-(cyclopentylideneamino)-4-oxo-2-(phenylimino)thiazolidin-5-ylidene)acetate (14) into the more stable (Z)-Methyl 2-[(Z)-2-(cyclopentylidenehydrazono)-4-oxo-3-phenylthiazolidin-5-ylidene]acetate (5a) was discussed and confirmed.

Keywords: alkylidene; behavior cyclic; hydrazinecarbothioamides cyclization; alkylidene hydrazinecarbothioamides; cyclic alkylidene; dimethyl acetylenedicarboxylate

Journal Title: Journal of Heterocyclic Chemistry
Year Published: 2017

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