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Regioselectivity of Alkylation of 3-Substituted 5-Amino-1,2,4-thiadiazoles

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

We have synthesized 3-substituted 4-alkyl-5-imino-4,5-dihydro-1,2,4-thiadiazoles by reaction of 3-alkyl(benzyl)thio-5-amino-1,2,4-thiadiazoles with methyl iodide or ethylene chlorohydrin. In the reaction with epichlorohydrin, addition of an oxirane molecule occurs with formation of tetrahydropyrimido[2,1-b]-1,2,4-thiadiazoles.

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REFERENCES

  1. F. Kurzer, in: Advances in Heterocyclic Chemistry, Ed. by A. R. Katritzky, Academic Press, New York (1982), Vol. 32, p. 378.

    Google Scholar 

  2. T. Kamiya, T. Naito, S. Negi, Y. Komatu, Y. Kai, T. Nakamura, I. Sumyama, E. Matida, S. Nomoto, K. Kitoh, K. Katsu, and H. Yamauti, Russian Federation Pat. 2010796; Byull.Izobret., No. 7, 67 (1994).

  3. C. Parkanyi, H. L. Yuan, N. S. Cho, J.-H. J. Jaw, T. E. Woodhouse, and T. L. Aung, J.Heterocycl.Chem., 26, 1331 (1989).

    Google Scholar 

  4. French Pat. 234545; Chem.Abstr., 89, 24322 (1978).

    Google Scholar 

  5. W. A. Gay, US Pat. 4343945; Chem.Abstr., 97,216193 (1985).

    Google Scholar 

  6. N. N. Mel'nikov, Pesticides.Chemistry, Technology, and Application [in Russian], Khimiya, Moscow (1987), p. 618.

    Google Scholar 

  7. J. Geordeler, A. Huppertz, and K. Wember, Chem.Ber., 87, 68 (1954).

    Google Scholar 

  8. L. Pentimalli, G. Milani, and F. Biavati, Gazz.Chim.Ital., 107, 1 (1977).

    Google Scholar 

  9. V. V. Klusis, Author's Abstract of Dissertation in competition for the academic degree of Candidate of Chemical Sciences, Riga (1965).

  10. R. Rastogi and S. Sharma, Synthesis, 861 (1983).

  11. A. A. Kremzer, Yu. V. Strokin, N. A. Klyuev, and V. P. Buryak, Khim.Geterotsikl.Soedin., 1102 (1981).

  12. R. F. Ambartsumov and L. P. Kosmacheva, Khim.Geterotsikl.Soedin., 993 (2001).

  13. D. Barton and W. D. Ollis, eds., Comprehensive Organic Chemistry [Russian translation], Khimiya, Moscow (1985), Vol. 9, p. 542.

    Google Scholar 

  14. F. N. Allen, O. Kennard, and D. G. Watson, J.Chem.Soc., Perkin Trans.2, No. 12, S1 (1987).

  15. J. Goerdeler and P. Linden, Chem.Ber., 89, 2742 (1956).

    Google Scholar 

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Authors and Affiliations

  1. Acad. S. Yunusov Institute of Chemistry of Plant Substances, Academy of Sciences of the Republic of Uzbekistan, Tashkent, 700170

    M. Khakimov, R. F. Ambartsumova, B. Tashkhodzhaev, M. Yu. Antipin & Kh. M. Shakhidoyatov

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  1. M. Khakimov
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  2. R. F. Ambartsumova
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  3. B. Tashkhodzhaev
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  4. M. Yu. Antipin
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  5. Kh. M. Shakhidoyatov
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Khakimov, M., Ambartsumova, R.F., Tashkhodzhaev, B. et al. Regioselectivity of Alkylation of 3-Substituted 5-Amino-1,2,4-thiadiazoles. Chemistry of Heterocyclic Compounds 37, 1005–1010 (2001). https://doi.org/10.1023/A:1012795819528

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