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4-Thionazolidones, derivatives and analogs

III. Synthesis and reactions of 4-thionthiazolid-2-one (isorhodanine)

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

A hitherto unknown isomer of rhodanine, 4-thiothiazolid-2-one (isorhodanine), is prepared by boiling thiazolidine-2, 4-dione with P2S5 in anhydrous dioxane for 3 hr. Isorhodanine I is characterized by great reactivity of the methylene and thione groups. The 4-phenylhydrazone and 4-phenylimino derivatives of I are prepared, as well as condensation products obtained by condensing I with aromatic aldehydes and diazonium salts. 5-Methylisorhodanine is also prepared. A derivative of I containing a quinoline ring is further obtained by reacting I with anthranilaldehyde.

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For Part II see [2].

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Grischuk, A.P., Komaritsa, I.D. & Baranov, S.N. 4-Thionazolidones, derivatives and analogs. Chem Heterocycl Compd 2, 541–543 (1966). https://doi.org/10.1007/BF00477515

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  • DOI: https://doi.org/10.1007/BF00477515

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