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Synthesis and Properties of sym-Triazine Derivatives. 18. Synthesis of N-Substituted 2,4-Diamino-6-(benzothiazolyl-2-thiomethyl)-sym-triazines

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The condensation of methyl benzothiazolyl-2-thioacetate with N-substituted biguanides in the presence of sodium methylate gave 2-amino-4-(RR'-amino)-6-(benzothiazolyl-2-thiomethyl)-sym-triazines. In a number of cases the 1,1-disubstituted 5-(benzothiazolyl-2-thioacetyl)biguanides could also be separated and these could be cyclized by refluxing in DMF to the corresponding substituted sym-triazines described. The latter type of compound was also synthesized by treating 2-amino-4-trichloromethyl-6-(benzothiazolyl-2-thiomethyl)-sym-triazine with primary and secondary aliphatic and heterocyclic amines or by the reaction of N-substituted 2,4-diamino-6-chloromethyl-sym-triazines with 2-mercaptobenzothiazole.

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REFERENCES

  1. V. I. Kelarev,V. N. Koshelev,N. V. Belov,R. A. Karakhanov, and O. V. Malova, Khim. Geterotsikl. Soedin., 667 (1995).

  2. C. F. Vaz,S. K. Bhumgara, and V. Nadkarny, Indian J. Chem., 14B, 709 (1976).

    Google Scholar 

  3. T. Dabhi,V. H. Shah, and A. R. Parkh, Indian J. Pharm. Sci. 54, 109 (1992).

    Google Scholar 

  4. P. S. Desai, and K. R. Desai, J. Indian Chem. Soc., 71, 155 (1994).

    Google Scholar 

  5. V. I. Kelarev,V. N. Koshelev,I. A. Golubeva, and O. V. Malova, Stabilizers and Modifiers of Organic Materials Based on sym-Triazine Derivatives, Central Scientific Research Institute for Petroleum Technology and Chemistry, Moscow (1996).

    Google Scholar 

  6. M. Camenzind, Eur. Pat. 5959771; Chem. Abstr., 112, 120434 (1994).

    Google Scholar 

  7. V. I. Kelarev,O. G. Gracheva,M. A. Silin,V. N. Koshelev, and I. A. Golubeva, Neftepererabotka i neftekhimiya, 29 (1997).

  8. V. I. Kelarev,I. A. Golubeva,O. G. Gracheva, and M. A. Silin, Neftepererabotka i neftekhimiya, 22 (1998).

  9. V. Nakamura,M. Saito, and K. Mori, Nippon Gomu Kyokaishi, 53, 244 (1980).

    Google Scholar 

  10. W. F. Beech, J. Chem. Soc. (C), 466 (1967).

  11. V. I. Kelarev,G. V. Morozova,V. N. Koshelev,N. V. Belov, and A. M. Kuatbekov, Izv. vuz. Khim. i khim. tekhnol., 40, 83 (1997).

    Google Scholar 

  12. V. I. Kelarev,R. A. Karakhanov,A. S. Kokosova, and G. D. Gankin, Khim. Geterotsikl. Soedin., 1250 (1992).

  13. V. N. Koshelev,V. I. Kelarev,R. A. Karakhanov, and S. N. Shalkarov, Zh. Org. Khim., 31, 291 (1995).

    Google Scholar 

  14. V. I. Kelarev,V. N. Koshelev,G. V. Morozova,R. A. Karakhanov, and A. S. Remizov, Khim. Geterotsikl. Soedin., 214 (1995).

  15. E. M. Smolin and L. Rappoport, s-Triazine and Derivatives, Interscience, New York, London (1959).

    Google Scholar 

  16. W. R. Sherman, J. Org. Chem., 26, 88 (1961).

    Google Scholar 

  17. V. I. Kelarev,A. Dibi, and A. F. Lunin, Khim. Geterotsikl. Soedin., 1557 (1985).

  18. V. I. Kelarev,F. Laauad Yakh'ya,R. A. Karakhanov,I. A. Golubeva,T. P. Vishnyakova, and O. V. Malova, Khim. Geterotsikl. Soedin., 681 (1988).

  19. A. I. Finkel'shtein and E. N. Boitsov, Usp. Khim., 31, 1496 (1962).

    Google Scholar 

  20. A. R. Katritzky (ed.), Physical Methods in the Chemistry of Heterocyclic Compounds [Russian translation], Mir, Moscow, Leningrad (1966).

    Google Scholar 

  21. V. E. Allenstein,W. Rodzum and H. Weidheim, Z. Anorg. Allg. Chem., 408, 53 (1974).

    Google Scholar 

  22. A. I. Finkel'shtein, Opt. i Spektrosk., 5, 264 (1959).

    Google Scholar 

  23. V. I. Kelarev,R. A. Karakhanov,Yu. N. Polivin,A. M. Kuatbekov,A. S. Remizov, and A. I. Mikaya, Khim. Geterotsikl. Soedin., 1271 (1993).

  24. A. I. Rutavichyus and S. P. Iokubaitite, Khim. Geterotsikl. Soedin., 40 (1984).

  25. M. I. Husain and V. Kumar, Indian J. Chem., 31B, 673 (1992).

    Google Scholar 

  26. S. L. Shapiro,V. A. Parrino, and L. Freedmann, J. Am. Chem. Soc., 81, 3728 (1959).

    Google Scholar 

  27. P. C. Das.B. B. Patra,A. N. Bose, and U. P. Basu, Indian J. Chem., 6, 691 (1968).

    Google Scholar 

  28. M. A. Silin,V. I. Kelarev,O. G. Gracheva,I. A. Golubeva, and N. A. Grigor'eva, Bashk. Khim. Zh., 5, 14 (1998).

    Google Scholar 

  29. S. L. Shapiro,E. Isaacs,V. A. Parrino, and L. Freedmann, J. Org. Chem., 25, 384 (1960).

    Google Scholar 

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  1. I. M. Gubkin State University for Oil and Gas, Moscow, 117917

    V. I. Kelarev, M. A. Silin & O. A. Borisova

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  1. V. I. Kelarev
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  2. M. A. Silin
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  3. O. A. Borisova
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Kelarev, V.I., Silin, M.A. & Borisova, O.A. Synthesis and Properties of sym-Triazine Derivatives. 18. Synthesis of N-Substituted 2,4-Diamino-6-(benzothiazolyl-2-thiomethyl)-sym-triazines. Chemistry of Heterocyclic Compounds 39, 632–639 (2003). https://doi.org/10.1023/A:1025102300933

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