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Synthesis of N-Substituted Derivatives of 3-(1,4-Benzodioxan-2-yl)-4-phenyl-1,2,4-triazole-5(4H)-thiones

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Abstract

The addition of 5-(1,4-benzodioxan-2-yl)-4-phenyl-4H-1,2,4-triazole-3-thiol to the C=C double bond of acrylonitrile, acrylamide, and ethyl acrylate afforded 3-[3-(1,4-benzodioxan-2-yl)-4-phenyl-5-sulfanylidene-4,5-dihydro-1H-1,2,4-triazol-1-yl]propanoic acid nitrile, amide, and ethyl ester. The latter was converted to the corresponding hydrazide which reacted with substituted benzoyl chlorides to give unsymmetrical diacylhydrazines, and their cyclization by the action of phosphoryl chloride in toluene afforded tricyclic products containing 1,4-benzodioxane, 1,2,4-triazole, and 1,3,4-oxadiazole heterocycles.

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Authors and Affiliations

  1. Scientific Technological Center of Organic and Pharmaceutical Chemistry, National Academy of Sciences of Armenia, 0014, Yerevan, Armenia

    S. O. Vardanyan, A. S. Avagyan, A. A. Aghekyan, A. B. Sargsyan & H. A. Panosyan

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  1. S. O. Vardanyan
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  2. A. S. Avagyan
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  3. A. A. Aghekyan
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  4. A. B. Sargsyan
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  5. H. A. Panosyan
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Correspondence to A. S. Avagyan.

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The authors declare no conflict of interest.

Additional information

Translated from Zhurnal Organicheskoi Khimii, 2021, Vol. 57, No. 7, pp. 967–972 https://doi.org/10.31857/S0514749221070065.

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Vardanyan, S.O., Avagyan, A.S., Aghekyan, A.A. et al. Synthesis of N-Substituted Derivatives of 3-(1,4-Benzodioxan-2-yl)-4-phenyl-1,2,4-triazole-5(4H)-thiones. Russ J Org Chem 57, 1068–1072 (2021). https://doi.org/10.1134/S107042802107006X

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  • DOI: https://doi.org/10.1134/S107042802107006X

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