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Efficient Catalytic and Thermal Syntheses of Novel Thiadiazole, Triazole, Benzothiazole, and Fused Quinazoline Derivatives

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Abstract

A thiourea derivative, 4-chloro-N-[(4-chlorophenyl)carbamothioyl]benzamide, was oxidized with iodine in acetic acid to give the corresponding disulfide, whereas its reaction with bromine in acetic acid produced 4-chloro-N-(6-chloro-1,3-benzothiazol-2-yl)benzamide. Thiadiazole derivative was obtained as a result of chlorination of the thiourea, followed by amination and subsequent intramolecular cyclodehydration. Triazole derivative was synthesized by the condensation of that thiourea with 2 equiv of hydrazine hydrate in ethanol. The thiourea derivative underwent cyclization on heating in N,N-dimethylformamide to generate intermediate 6-chloro-4-(chlorophenyl)quinazoline-2(1H)-thione which reacted with nitrogen and carbon nucleophiles such as semicarbazide, thiosemicarbazide, urea, diethyl succinate, and diethyl malonate to afford fused triazoloquinazoline, pyroloquinazoline, and some other quinazoline derivatives.

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Authors and Affiliations

  1. Chemistry Department, Faculty of Science, Zagazig University, 44519, Zagazig, Egypt

    M. H. M. Abd El-Azim, M. G. Assay, W. Farid & A. M. Abdel Hamid

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  1. M. H. M. Abd El-Azim
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  2. M. G. Assay
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  3. W. Farid
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  4. A. M. Abdel Hamid
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Correspondence to M. H. M. Abd El-Azim.

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El-Azim, M.H.M.A., Assay, M.G., Farid, W. et al. Efficient Catalytic and Thermal Syntheses of Novel Thiadiazole, Triazole, Benzothiazole, and Fused Quinazoline Derivatives. Russ J Org Chem 58, 597–603 (2022). https://doi.org/10.1134/S1070428022040194

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