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Synthetic Development and Assessment of Antioxidant Activity of Imino[1,2,4]triazolo[1,5-a]pyrimidine-6-carbonitrile and Its Derivatives

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Abstract

The reaction of 2-[bis(methylsulfanyl)methylidene]malononitrile with 1H-1,2,4-triazol-3-amine in N,N-dimethylformamide in the presence of anhydrous potassium carbonate led to the formation of 7-imino-5-(methylsulfanyl)-1,7-dihydro[1,2,4]triazolo[1,5-a]pyrimidine-6-carbonitrile. The latter was then reacted with some nitrogen and carbon nucleophiles such as substituted anilines and active methylene compounds to afford the corresponding 5-substituted derivatives. The structure of the synthesized compounds was confirmed by IR, NMR, and mass spectra and elemental analyses. Furthermore, their potential as antioxidant agents was evaluated using DPPH and hydroxyl radical scavenging assays.

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ACKNOWLEDGMENTS

The authors duly acknowledge the Principal, Yeshwant Mahavidyalaya, Nanded, for providing laboratory facilities. V.N.B. is thankful to SRTMU, Nanded, for sanctioning a grant of MRP (APDS/Univ. MRP/Sci. and Tech. Chemistry/2019-20/2819). The authors also express their gratitude to the Director, CSIR-IICT Hyderabad, Vishnu Chemicals Pvt. Ltd., Hyderabad, and Punjab University, Chandigarh, for providing help with the analysis of spectral data.

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Authors and Affiliations

  1. P.G. Research Centre, Department of Chemistry, M.S.G. College Malegaon, 423105, Malegaon, Maharashtra, India

    N. B. Wadwale

  2. Centre for Nano and Material Science, JAIN University, 562112, Bangalore, Karnataka, India

    D. Prasad & A. H. Jadhav

  3. Department of Chemistry, M. G. M. Ahmedpur, 413515, Ahmdepur, Latur District, Maharashtra, India

    A. R. Karad

  4. Department of Chemistry, D. A. B. N. College, 415408, Chikhali, Sangli District, Maharashtra, India

    G. S. Khansole

  5. Department of Chemistry, S. D. College, 431120, Soegaon, Aurangabad District, Maharashtra, India

    S. S. Choudhare

  6. P.G. Research Centre, Department of Chemistry, Yeshwant Mahavidyalay Nanded, 431602, Nanded, Maharashtra, India

    S. V. Navhate & V. N. Bhosale

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Wadwale, N.B., Prasad, D., Jadhav, A.H. et al. Synthetic Development and Assessment of Antioxidant Activity of Imino[1,2,4]triazolo[1,5-a]pyrimidine-6-carbonitrile and Its Derivatives. Russ J Org Chem 57, 2031–2038 (2021). https://doi.org/10.1134/S1070428021120204

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