Skip to main content

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

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.

This is a preview of subscription content, access via your institution.

Figure 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.

  2. Abbott GmbH & Co. KG DE Patent 10259382.

  3. Ouf, N. H.; Amr, A. E. Monatsh. Chem. 2008, 139, 579.

    Article  CAS  Google Scholar 

  4. Eichenberger, K.; Schmidt, P.; Schweizer, E. DE Patent 1937459.

  5. Steiner, G.; Lubisch, W.; Bach, A.; Emling, F.; Wicke, K.; Teschendorf, H.-J.; Behl, B.; Kerrigan, F.; Cheetham, S. DE Patent 19636769.

  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.]

    Article  CAS  Google Scholar 

  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.]

    Article  CAS  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  9. Kovaleva, S. A. Diss. Cand. Chem. Sci., Moscow, 2011.

  10. Sheldrick, G. M. Acta Crystallogr., Sect. A: Found Crystallogr. 2008, A64, 112.

    Article  Google Scholar 

Download references

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

Author information

Authors and Affiliations


Corresponding author

Correspondence to Leonid G. Voskressensky.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2015, 51(1), 17–25

Electronic supplementary material

Below is the link to the electronic supplementary material.


(PDF 271 kb)

Rights and permissions

Reprints and Permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Voskressensky, L.G., Kovaleva, S.A., Borisova, T.N. et al. Synthesis of 2-(chloro(methoxy, morpholino)methyl)-hexahydropyrimidothieno[3,2-c]azocines and tetrahydrospiro[pyrido[4,5']thieno[2,3-d]pyrimidines]. Chem Heterocycl Comp 51, 17–25 (2015).

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: