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Acyl Isothiocyanates of 2-Allyl- and 2-Benzylmaleopimarimide: Synthesis of 1,3,4-Thiadiazoles

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Abstract

New linear hydrazinocarbonothioyl derivatives of maleopimarimides were synthesized in high yields by the interaction of acyl isothiocyanates of 2-allyl- and 2-benzylmaleopimarimides with acetohydrazide and hydrazide of 4-methoxybenzoic acid. 1,3,4-Thiadiazole derivatives were synthesized by boiling hydrazinocarbonothioyl derivatives of maleopimarimides with a catalytic amount of concentrated H2SO4 in ethanol. The structure of the synthesized compounds was determined using 1H,13C NMR, 1H–13C HSQC, 1H–13C HMBC, COSY, NOESY, and 1H-15N HMBC spectroscopy methods.

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Funding

The work was supported by the State Assignment (no. 1021062311395-6–1.4.1 “Synthesis of biologically active substances based on natural compounds. Creation of environmentally friendly materials and technologies”).

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Correspondence to G. F. Vafina.

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Vafina, G.F., Poptsov, A.I. Acyl Isothiocyanates of 2-Allyl- and 2-Benzylmaleopimarimide: Synthesis of 1,3,4-Thiadiazoles. Russ J Gen Chem 94, 514–521 (2024). https://doi.org/10.1134/S1070363224030034

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