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Intramolecular cyclization of 5-amino-4-bis (β-chloroethyl)aminopyrimidines

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

4-R-5,6,7,8,9,10-Hexahydroimidazo [1,2,3-i,j] pteridinium chlorides and 4-R-7-(β-chloroethyl)-7,8-dihydroimidazo[1,2-c]pyrimidinium chlorides were obtained in the reaction of 6-R-5-amino-4-bis(β-hydroxyethyl) aminopyrimidines (R = H, Cl) with SOCl2 or POCl3. The pteridinium chlorides are formed through cyclization of the intermediately formed 4-R-8-(β-chloroethyl)-5,6,7,8-tetrahydropteridines, which, for R = Cl, were obtained independently by reduction of 4-chloro-6-bis-(β-chloroethyl) amino-5-nitropyrimidine. The conditions for the cyclization of imidazopyrimidinium chlorides to give imidazopteridinium chlorides were investigated.

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Literature cited

  1. G. V. Shishkin and G. A. Zloba, USSR Inventor's Certificate No. 749385; Byull. Izobret., No. 27, 101 (1980).

  2. G. V. Shishkin and A. A. Gall', Khim. Geterotsikl. Soedin., No. 6, 831 (1980).

    Google Scholar 

  3. A. A. Gall' and G. V. Shishkin, Khim. Geterotsikl. Soedin., No. 5, 677 (1983).

    Google Scholar 

  4. G. R. Ramage and G. Trappe, J. Chem. Soc., No. 11, 4410 (1952).

    Google Scholar 

  5. J. Clark and G. R. Ramage, J. Chem. Soc., No. 8, 2821 (1958).

    Google Scholar 

  6. J. H. Lister, J. Chem. Soc., No. 2, 899 (1960).

    Google Scholar 

  7. R. C. Elderfild and R. N. Prasad, J. Org. Chem., 25, 1583 (1960).

    Google Scholar 

  8. B. A. Ivin and V. G. Nemets, Zh. Obshch. Khim., 35, 1303 (1965).

    Google Scholar 

  9. K. L. Nagpal and M. M. Dhar, Tetrahedron, 23, 1297 (1967).

    Google Scholar 

  10. L. D. Protsenko and Yu. I. Bogodist, Ukr. Khim. Zh., 36, 1043 (1970).

    Google Scholar 

  11. A. F. Vlasenko, B. E. Mandrichenko, G. K. Rogul'chenko, R. S. Sinyak, I. A. Mazur, and P. M. Kochergin, Khim. Geterotsikl. Soedin., No. 6, 834 (1976).

    Google Scholar 

  12. T. Ueda and J. J. Fox, J. Am. Chem. Soc., 85, 4024 (1963).

    Google Scholar 

  13. M. Yanai, S. Takeda, T. Baba, and K. Titagawa, Yakugaku Zasshi, 94, 1503 (1974); Chem. Abstr., 82, 140054 (1975).

    Google Scholar 

  14. J. Clark and M. Curphey, J. Chem. Soc., Perkin I, No. 16, 1855 (1977).

    Google Scholar 

  15. P. R. Brook and G. R. Ramage, J. Chem. Soc., No. 3, 896 (1955).

    Google Scholar 

  16. W. R. Boon, W. G. M. Jones, and G. R. Ramage, J. Chem. Soc., No. 1, 96 (1951).

    Google Scholar 

  17. B. Bobranski and K. Stankiewicz, Roczn. Chem., 45, 277 (1971).

    Google Scholar 

  18. L. D. Protsenko and Yu. I. Bogodist, Zh. Obshch. Khim., 33, 537 (1963).

    Google Scholar 

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1406–1413, October, 1983.

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Naumenko, I.I., Shishkin, G.V. Intramolecular cyclization of 5-amino-4-bis (β-chloroethyl)aminopyrimidines. Chem Heterocycl Compd 19, 1120–1127 (1983). https://doi.org/10.1007/BF00505771

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  • DOI: https://doi.org/10.1007/BF00505771

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