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Heterocyclic Synthesis with 4-Benzoyl-1-cyanoacetylthiosemicarbazide: Selective Synthesis of Some Thiazole, Triazole, Thiadiazine, Pyrrylthiazole, and Pyrazolo[1,5-a]triazine Derivatives

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Summary.

4-Benzoyl-1-cyanoacetylthiosemicarbazide undergoes coupling reaction with aromatic diazonium chloride to afford (arylhydrazono)thiosemicarbazide, which was reacted with phenacyl bromide regioselectivity to afford the thiazoline. The (arylhydrazono)thiosemicarbazide could be transformed into the pyrazolo[1,5-a]triazine. Heterocyclization of 4-benzoyl-1-cyanoacetylthiosemicarbazide with α-haloketones (bromoacetone and phenacyl bromide), ethyl iodide, and ethyl bromoacetate furnished the pyrrylthiazoles, 1,2,4- triazole, and 1,3,4-thiadiazine. The latter was coupled with aromatic diazonium chloride to give the bis(arylhydrazono)‐thiadiazine. The mechanism for the formation of the title compounds was suggested and discussed.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Mansoura University, Mansoura, Egypt

    Samir Bondock, Abd El-Gaber Tarhoni & Ahmed A. Fadda

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  1. Samir Bondock
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  2. Abd El-Gaber Tarhoni
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  3. Ahmed A. Fadda
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Correspondence to Samir Bondock.

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Bondock, S., Tarhoni, AG. & Fadda, A. Heterocyclic Synthesis with 4-Benzoyl-1-cyanoacetylthiosemicarbazide: Selective Synthesis of Some Thiazole, Triazole, Thiadiazine, Pyrrylthiazole, and Pyrazolo[1,5-a]triazine Derivatives. Monatsh Chem 139, 153–159 (2008). https://doi.org/10.1007/s00706-007-0764-5

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  • DOI: https://doi.org/10.1007/s00706-007-0764-5

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