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Purines, Pyrimidines, and Condensed Systems Based on them. 18. Reaction of 6,8-Dimethylpyrimido[4,5-c]pyridazine-5,7(6H,8H)dione N(2)-oxide with Alkylamines

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Abstract

Heating 6,8-dimethylpyrimido[4,5-c]pyridazine-5,7(6H,8H)-dione N(2)-oxide (2) with piperidine or morpholine gave a moderate yield of 3-piperidino- and 3-morpholino-6,8-dimethylpyrimido[4,5-c]pyridazine-5,7(6H,8H)-diones (3a,b). Reaction of N-oxide (2) with ammonia and alkylamines in the presence of an oxidant led to formation of the 3-amino derivatives of 2 and the corresponding desoxy products 3. The latter were also obtained by an independent method by heating 3-chloro-6,8-dimethylpyrimido[4,5-c]pyridazine-5,7(6H,8H)-dione with alkylamines in butanol.

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REFERENCES

  1. A. V. Gulevskaya, V. V. Goryunenko, and A. F. Pozharskii, Khim. Geterotsikl. Soedin., 1113 (2000).

  2. A. V. Gulevskaya, D. V. Besedin, and A. F. Pozharskii, Izvest. Akad. Nauk, Ser. Khim., 1161 (1999).

  3. O. N. Chupakhin, V. N. Charushin, and H. C. van der Plas, Nucleophilic Aromatic Substitution of Hydrogen. Acad. Press, San Diego, 1994, 367.

    Google Scholar 

  4. A. Rykowski and H. C. van der Plas, Synthesis, 844 (1985).

  5. H. Tondys and H. C. van der Plas, J. Heterocycl. Chem., 23, 621 (1986).

    Google Scholar 

  6. Y. Tagawa, T. Yoshida, N. Honjo, and Y. Goto, Heterocycles, 29, 1781 (1989).

    Google Scholar 

  7. V. Pfleiderer, Khim. Geterotsikl. Soedin., 1299 (1974).

  8. W. Pfleiderer and H. Ferch, Ann., 615, 48 (1958).

    Google Scholar 

  9. S. Nishigaki, M. Ichiba, and K. Senga, J. Org. Chem., 48, 1628 (1983).

    Google Scholar 

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Authors and Affiliations

  1. Rostov State University, Rostov-on-Don, 344090, Russia

    D. V. Besedin, A. V. Gulevskaya & A. F. Pozharskii

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  1. D. V. Besedin
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  2. A. V. Gulevskaya
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  3. A. F. Pozharskii
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Besedin, D.V., Gulevskaya, A.V. & Pozharskii, A.F. Purines, Pyrimidines, and Condensed Systems Based on them. 18. Reaction of 6,8-Dimethylpyrimido[4,5-c]pyridazine-5,7(6H,8H)dione N(2)-oxide with Alkylamines. Chemistry of Heterocyclic Compounds 36, 1213–1218 (2000). https://doi.org/10.1023/A:1002829018667

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  • DOI: https://doi.org/10.1023/A:1002829018667

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