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Formation of imidazolidine derivatives from dimethyl (2,2-dimethylhydrazino)succinate in reactions with allyl and phenyl isothiocyanates

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The reaction of (2,2-dimethylhydrazino)succinic acid ester with allyl and phenyl isothiocyanates leads to esters of 1-substituted (3-dimethylamino-5-oxo-2-thioxo-4-imidazolidinyl)acetic acids, which in protic solvents undergo a slight degree of elimination of dimethylamine to give esters of 1-substituted (5-oxo-2-thioxoimidazolidin-4-ylidene)acetic acids. The structure of methyl (1-allyl-5-oxo-2-thioxoimidazolidin-4-ylidene)acetate was proved by x-ray diffraction analysis.

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Literature Cited

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Communication 3 from the series “Derivatives of hydrazino carboxylic acids,” See [1] for communication 2.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1219–1223, September, 1987.

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Bremanis, G.A., Kemme, A.A., Kalvin'sh, I.Y. et al. Formation of imidazolidine derivatives from dimethyl (2,2-dimethylhydrazino)succinate in reactions with allyl and phenyl isothiocyanates. Chem Heterocycl Compd 23, 974–978 (1987). https://doi.org/10.1007/BF00475363

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  • DOI: https://doi.org/10.1007/BF00475363

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