Skip to main content
SpringerLink
Log in

Some Transformations of 3-(2,2-Dimethyltetrahydro-2H-pyran-4-yl-2-thioxo-2,3-dihydro-1H-spiro(benzo[h]quinazoline-5,1'-cycloheptan)-4(6H)-one

  • Published:
Russian Journal of Organic Chemistry Aims and scope Submit manuscript

Abstract

Starting from 3-(2,2-dimethyltetrahydro-2H-pyran-4-yl)-2-thioxo-2,3-dihydro-1H-spiro(benzo[h]quinazoline-5,1'-cycloheptan)-4(6H)-one, a series of dibenzo[h]quinazolines was synthesized, in which the spiro(benzo[h]quinazoline-5,1'-cycloheptan)-4(6H)-one moiety in the second position of the –SCH2-group is linked to benzo[h]quinazolines of various structures (spirocyclic and non-spirocyclic). 2-Thioxobenzo[h]quinazoline was converted to a 2-hydrazinyl derivative, whose base-catalyzed hydrazinolysis led to 3-(2,2-dimethyltetrahydro-2H-pyran-4-yl)-3H-spiro(benzo[h]quinazoline-5,1'-cycloheptan)-4(6H)-one. 2-Hydrazinylbenzo[h]quinazoline was reacted with acetone, benzaldehyde, and benzoyl isothiocyanate to obtain hydrazones and thiosemicarbazide. Methods for the synthesis of 4-(2,2-dimethyltetrahydro-2H-pyran-4-yl)-4H-spiro(benzo[h][1,2,4]triazolo[4,3-a]quinazoline-6,1'-cycloheptan)-5(7H)-one and 4-(2,2-dimethyltetrahydro-2H-pyran-4-yl)-1-sulfanyl-4H-spiro(benzo[h][1,2,4]triazolo[4,3-a]quinazoline-6,1'-cycloheptan)-5(7H)-one were developed. Alkylation of the latter gave 1-sulfanyl-substituted 4-(2,2-dimethyltetrahydro-2H-pyran-4-yl)-4H-spiro(benzo[h][1,2,4]triazolo[4,3-a]quinazoline-6,1'-cycloheptan)-5(7H)-ones.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Scheme
Scheme

Similar content being viewed by others

REFERENCES

  1. Maurya, H.K., Hasanain, M., Singh, S., Sarkar, J., Dubey, V., Shukla, A., Luqman, S., Khanc, F., and Gupta, A., RSC Adv., 2016, vol. 22, p. 18607.

    Article  Google Scholar 

  2. Wu, L. and Zhang, Ch., RSC Adv., 2016, vol. 34, p. 287555. https://doi.org/10.1039/C6RA03323G

    Article  CAS  Google Scholar 

  3. Keshari, A.K., Singh, A.K., Raj, V., Rai, A., Trivedi, P., Ghosh, B., Kumar, U., Rawat, A., Kumar, D., and Saha, S., Drug Des. Devel. Ther., 2017, vol. 11, p. 1623. https://doi.org/10.2147/DDDT.S136692

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  4. Sati, N., Kumar, S., and Rawat, M.S., Ind. J. Pharm. Sci., 2009, vol. 71, p. 572.

    Article  CAS  Google Scholar 

  5. Sahoo, M., Jena, L., Daf, S., and Kumar, S., Genomics Inform., 2016, vol. 14, p. 104. https://doi.org/10.5808/GI.2016.14.3.104

    Article  PubMed  PubMed Central  Google Scholar 

  6. Gomha, S.M., Abbas, E.M.H., and Farghaly, T., J. Het. Chem., 2017, vol. 54, p. 610. https://doi.org/10.1002/jhet.2632

    Article  CAS  Google Scholar 

  7. Maurya, H.K., Verma, R., Alam, S., Pandey, Sh., Pathak, V., Harma, S., Srivastava, K.K., Neg, A.S., and Gupta, A., Bioorg Med. Chem. Lett., 2013, vol. 23, p. 5844. https://doi.org/10.1016/j.bmcl.2013.08.101

    Article  CAS  PubMed  Google Scholar 

  8. Ebied, M.Y., Zaghary, W.A., Amin, K.M., and Hammad, Sh.F., J. Adv. Pharm. Res., 2017, vol. 1, p. 216. https://doi.org/10.21608/aprh.2017.4043

    Article  Google Scholar 

  9. Markosyan, A.I., Hakopyan, Kh.S., Ayvazyan, A.S., Mamyan, S.S., Ayvazyan, A.G., Tamazyan, R.A., Arsenyan, F.H., and Avakimyan, J.A., Chem. J. Armenia, 2018, vol. 71, p. 596.

    CAS  Google Scholar 

  10. Markosyan, A.I., Hayrapetyan, K.K., Gabrielyan, S.H., Shirinyan, V.Z., Mamyan, S.S., Avakimyan, J.A., and Stepayan, G.M., Russ. J. Org. Chem., 2018, vol. 54, p. 606. https://doi.org/10.1134/S1070428018040152

    Article  CAS  Google Scholar 

  11. Markosyan, A.I., Dilanyan, S.V., Sukasyan, R.S., Arsenyan, F.G., and Garibdzhaanyan, B.T., Pharm. Chem. J., 2008, vol. 42, p. 118. https://doi.org/10.1007/s11094-008-0079-9

    Article  CAS  Google Scholar 

  12. Markosyan, A.I., Oganisyan, M.G., Kuroyan, R.A., and Grigoryan, R.T., Arm. Khim. Zh., 1992, vol. 45, p. 208.

    Google Scholar 

  13. Markosyan, A.I., Ayvazyan, A.S., Gabrielyan, S.H., Mamyan, S.S., Arsenyan, F.H., Safaryan, A.S., and Arakelyan, H.H., Pharm. Chem. J., 2021, vol. 55, p. 133. https://doi.org/10.1007/s11094-021-02392-2

    Article  CAS  Google Scholar 

  14. Markosyan, A.I., Ayvazyan, A.S., Gabrielyan, S.A., and Mamyan, S.S., Russ. J. Org. Chem., 2021, vol. 57, p. 383. https://doi.org/10.1134/S107042802103009X

    Article  CAS  Google Scholar 

  15. Rukovodstvo po provedeniyu doklinicheskikh issledovanii lekarstvennykh sredstv (Guidelines for Conducting Preclinical Studies of Drugs), Mironov, A.N., Ed., Moscow: Meditsina, 2012.

Download references

Author information

Authors and Affiliations

  1. Scientific and Technological Center of Organic and Pharmaceutical Chemistry, National Academy of Sciences of the Republic of Armenia, 0014, Yerevan, Armenia

    A. I. Markosyan, A. S. Ayvazyan, S. H. Gabrielyan & S. S. Mamyan

Authors
  1. A. I. Markosyan
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. S. Ayvazyan
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. S. H. Gabrielyan
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. S. S. Mamyan
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to A. I. Markosyan.

Ethics declarations

The authors declare no conflict of interest.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Markosyan, A.I., Ayvazyan, A.S., Gabrielyan, S.H. et al. Some Transformations of 3-(2,2-Dimethyltetrahydro-2H-pyran-4-yl-2-thioxo-2,3-dihydro-1H-spiro(benzo[h]quinazoline-5,1'-cycloheptan)-4(6H)-one. Russ J Org Chem 58, 200–208 (2022). https://doi.org/10.1134/S1070428022020075

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428022020075

Keywords:

Search

Navigation