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Chemistry of Heterocyclic Compounds

, Volume 51, Issue 1, pp 17–25 | Cite as

Synthesis of 2-(chloro(methoxy, morpholino)methyl)-hexahydropyrimidothieno[3,2-c]azocines and tetrahydrospiro[pyrido[4,5']thieno[2,3-d]pyrimidines]

  • Leonid G. Voskressensky
  • Svetlana A. Kovaleva
  • Tatiana N. Borisova
  • Alexander A. Titov
  • Flavien Toze
  • Anna V. Listratova
  • Viktor N. Khrustalev
  • Alexey V. Varlamov
Articles

2-(Chloromethyl)-5,6,7,8-tetrahydropyrido[4',3':4,5]thieno[2,3-d]pyrimidin-4(3Н)-ones reacted with acetylenedicarboxylate ester, methyl propiolate or acetylacetylene, forming mixtures of 2-(chloromethyl)-5,6,7,10-tetrahydropyrimido[5',4':4,5]thieno[3,2-d]azocin-4(3Н)-ones and 2'-chloromethyl-6'-methylidene-2,3-dihydro-1Н-spiro[pyrido[4,5']thieno[2,3-d]pyrimidin]-4'(3'H)-ones in various ratios. Analogous products were also obtained in the reaction of 2-(methoxymethyl) derivative with methyl propiolate, while using 2-[(morpholin-4-yl)-methyl] derivative in a similar reaction led to the formation of a more complex product mixture.

Keywords

acetylacetylene dimethyl acetylenedicarboxylate methyl propiolate pyridothienopyrimidines pyrimidothieno[3,2-d]-azocines spiro[pyridine[4,5']thieno[2,3-d]pyrimidines] domino reactions recyclization 

Notes

This work received financial support from the Russian Foundation for Basic Research (grant 14-03-00311а).

Supplementary material

10593_2015_1652_MOESM1_ESM.pdf (272 kb)
ESM 1 (PDF 271 kb)

References

  1. 1.
    Steiner, G.; Schellhaas, K.; Lubisch, W.; Holzenkamp, U.; Starck, D.; Knopp, M.; Szabo, L.; Emling, F.; Garcia-Ladona, F. J.; Hofmann, H.-P.; Unger, L. DE Patent 19900545.Google Scholar
  2. 2.
    Abbott GmbH & Co. KG DE Patent 10259382.Google Scholar
  3. 3.
    Ouf, N. H.; Amr, A. E. Monatsh. Chem. 2008, 139, 579.CrossRefGoogle Scholar
  4. 4.
    Eichenberger, K.; Schmidt, P.; Schweizer, E. DE Patent 1937459.Google Scholar
  5. 5.
    Steiner, G.; Lubisch, W.; Bach, A.; Emling, F.; Wicke, K.; Teschendorf, H.-J.; Behl, B.; Kerrigan, F.; Cheetham, S. DE Patent 19636769.Google Scholar
  6. 6.
    Voskressensky, L. G.; Borisova, T. N.; Kovaleva, S. A.; Listratova, A. V.; Kulikova, L. N.; Khrustalev, V. N.; Ovcharov, M. V.; Varlamov, A. V. Russ. Chem. Bull., Int. Ed. 2012, 61, 370. [Izv. Akad. Nauk, Ser. Khim. 2012, 368.]CrossRefGoogle Scholar
  7. 7.
    Voskressensky, L. G.; Borisova, T. N.; Ovcharov, M. V.; Kulikova, L. N.; Sorokina, E. A.; Borisov, R. S.; Varlamov, A. V. Chem. Heterocycl. Compd. 2008, 44, 1510. [Khim. Geterotsikl. Soedin. 2008, 1861.]CrossRefGoogle Scholar
  8. 8.
    Bogolubsky, A. V.; Ryabukhin, S. V.; Stetsenko, S. V.; Chupryna, A. A.; Volochnyuk, D. M.; Tolmachev, A. A. J. Comb. Chem. 2007, 9, 661.CrossRefGoogle Scholar
  9. 9.
    Kovaleva, S. A. Diss. Cand. Chem. Sci., Moscow, 2011.Google Scholar
  10. 10.
    Sheldrick, G. M. Acta Crystallogr., Sect. A: Found Crystallogr. 2008, A64, 112.CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 2015

Authors and Affiliations

  • Leonid G. Voskressensky
    • 1
  • Svetlana A. Kovaleva
    • 1
  • Tatiana N. Borisova
    • 1
  • Alexander A. Titov
    • 1
  • Flavien Toze
    • 2
  • Anna V. Listratova
    • 1
  • Viktor N. Khrustalev
    • 3
  • Alexey V. Varlamov
    • 1
  1. 1.Peoples’ Friendship University of RussiaMoscowRussia
  2. 2.University of Douala, Faculty of Science, Department of ChemistryDoualaRepublic of Cameroon
  3. 3.A. N. Nesmeyanov Institute of Organoelement CompoundsRussian Academy of SciencesMoscowRussia

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