Skip to main content
SpringerLink
Log in

Some Transformations of 2-(Chloromethyl)-5,5-dimethyl-5,6-dihydrobenzo[h]quinazolin-4(3H)-one

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

Abstract

The condensation of 1-amino-3,3-dimethyl-3,4-dihydronaphthalene-2-carbonitrile with chloroacetyl chloride afforded chloro-N-(2-cyano-3,3-dimethyl-3,4-dihydronaphthalen-1-yl)acetamide which underwent cyclization to 2-(chloromethyl)-5,5-dimethyl-5,6-dihydrobenzo[h]quinazolin-4(3H)-one. The latter reacted with various nucleophiles (alkali metal alkoxides, piperazine, 2-sulfanylethanol) to give 2-(alkoxymethyl)-, 2-(piperazin-1-ylmethyl)-, and 2-{[(2-hydroxyethyl)sulfanyl]methyl}-5,5-dimethyl-5,6-dihydrobenzo[h]quinazolin- 4(3H)-ones. The condensation of 2-(chloromethyl)benzo[h]quinazoline with 2-thioxo derivatives of quinazoline and benzo[h]quinazolines led to the formation of bis-quinazolines in which 5,5-dimethyl-5,6- dihydrobenzo[h]quinazolin-4(3H)-one fragment is linked to quinazoline or benzo[h]quinazoline system through a CH2S bridge.

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

Similar content being viewed by others

References

  1. Sati, N., Kumar, S., and Rawat, M.S.M., Indian J. Pharm. Sci., 2009, vol. 71, no. 5, p. 572.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  2. Amr, A.-G.E., Sayed, H.H., and Abdulla, M.M., Arch. Pharm., 2005, vol. 338, p. 9433.

    Article  CAS  Google Scholar 

  3. Ohtomo, H., Tagata, T., Sasaki, K., Hirota, T., and Okuda, K., Tetrahedron, 2007, vol. 63, no. 51, p. 12 541.

    Article  CAS  Google Scholar 

  4. Sovadinová, I., Bláha, L., Janošek, J., Hilscherová, K., Giesy, J.P., Jones, P.D., and Holoubek, I., Environ. Toxicol. Chem., 2006, vol. 25, no. 5, p. 1291.

    Article  PubMed  Google Scholar 

  5. Liang, J.L., Park, S.E., Kwon, Y., and Jahng, Y., Bioorg. Med. Chem. Res., 2012, vol. 20, no. 16, p. 4962.

    Article  CAS  Google Scholar 

  6. Wissner, A., Floyd, M., Johnson, B.D., Fraser, H., Ingalls, C., Nittoli, T., Dushin, R.G., Discafani, C., Nilakantan, R., Marini, J., Ravi, M., Cheung, K., Tan, X., Musto, S., Annable, T., Siegel, M.M., and Loganzo, F., J. Med. Chem., 2005, vol. 48, no. 24, p. 7560.

    Article  CAS  PubMed  Google Scholar 

  7. Kidwai, M., Bhatnagar, D., Kumar, R., and Luthra, P.M., Chem. Pharm. Bull., 2010, vol. 58, no. 10, p. 1320.

    Article  CAS  PubMed  Google Scholar 

  8. Eathiraj, S., Palma, R., Hirschi, M., Volckova, E., Nakuci, E., Castro, J., Chen, C.-R., Chan, T.C.K., France, D.S., and Ashwell, M.A., J. Biol. Chem., 2011, vol. 286, p. 20 677.

    Article  CAS  Google Scholar 

  9. Wu, L., Zhang, Ch., and Li, W., Bioorg. Med. Chem. Lett., 2013, vol. 23, no. 17, p. 5002.

    Article  CAS  PubMed  Google Scholar 

  10. Brullo, C., Rocca, M., Fossa, P., Cichero, E., Barocelli, E., Ballabeni, V., Flammini, L., Giorgio, C., Saccani, F., Domenichini, G., and Brono, O., Bioorg. Med. Chem. Lett., 2012, vol. 22, p. 1125.

    Article  CAS  PubMed  Google Scholar 

  11. Gupta, R. and Chaudhary, R.P., Phosphorus, Sulfur Silicon Relat. Elem., 2012, vol. 187, no. 6, p. 735.

    Article  CAS  Google Scholar 

  12. Maurya, H.K., Vema, R., Alam, S., Pandey, Sh., Pathak, V., Shama, S., Srivastava, K.K. Negi, A.S., and Gupta, A., Bioorg. Med. Chem. Lett., 2013, vol. 23, no. 21, p. 5844.

    Article  CAS  PubMed  Google Scholar 

  13. Velpula, R., Banothu, J., Gali, R., Sargam, Y., and Bavantula, R., Turk. J. Chem., 2015, vol. 39, p. 620.

    Article  CAS  Google Scholar 

  14. Pathak, V., Maurya, H.K., Sharma, S., Srivastava, K.K., and Gupta, A., Bioorg. Med. Chem. Lett., 2014, vol. 24, no. 13, p. 2892.

    Article  CAS  PubMed  Google Scholar 

  15. Markosyan, A.I., Torshirzad, N.M., Gabrielyan, S.A., and Avakimyan, Dzh.A., Khim. Zh. Arm., 2013, vol. 66, no. 2, p. 303.

    CAS  Google Scholar 

  16. Markosyan, A.I., Hayrapetyan, K.K., Gabrielyan, S.H., Mamyan, S.S., and Avakimyan, J.A., Electron. J. Nat. Sci., 2016, vol. 2, no. 27, p. 3.

    Google Scholar 

  17. Markosyan, A.I., Torshirzad, N.M., Shakhbazyan, G.H., and Arsenyan, F.G., Pharm. Chem. J., 2014, vol. 47, no. 12, p. 651.

    Article  CAS  Google Scholar 

  18. Markosyan, A.I., Akalyan, Kh.S., Arsenyan, F.G., Sukasyan, R.S., and Garibdzhanyan, B.T., Pharm. Chem. J., 2008, vol. 42, no. 6, p. 313.

    Article  CAS  Google Scholar 

  19. Markosyan, A.I., Gabrielyan, S.A., Arsenyan, F.G., Sukasyan, R.S., and Sarkisyan, I.S., Pharm. Chem. J., 2010, vol. 44, no. 8, p. 409.

    Article  CAS  Google Scholar 

  20. Markosyan, A.I., Dilanyan, S.V., Kuroyan, R.A., Chachoyan, A.A., and Garibdzhanyan, B.T., Pharm. Chem. J., 1995, vol. 29, no. 4, p. 259.

    Article  Google Scholar 

  21. Rukovodstvo po provedeniyu doklinicheskikh issledovanii lekarstvennykh sredstv (A Guide to Preclinical Trials of Medicines), Mironov, A.N., Ed., Moscow: Grif i K, 2012, part 1, p. 509.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Scientific Technological Center of Organic and Pharmaceutical Chemistry, National Academy of Sciences of Armenia, pr. Azatutyan 26, Yerevan, 0014, Armenia

    A. I. Markosyan, K. K. Hayrapetyan, S. H. Gabrielyan, S. S. Mamyan, J. A. Avakimyan & G. M. Stepanyan

  2. Zelinskii Institute of Organic Chemistry, Russian Academy of Sciences, Leninskii pr. 47, Moscow, 119991, Russia

    V. Z. Shirinyan

Authors
  1. A. I. Markosyan
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. K. K. Hayrapetyan
    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. V. Z. Shirinyan
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. S. S. Mamyan
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. J. A. Avakimyan
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. G. M. Stepanyan
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to A. I. Markosyan.

Additional information

Original Russian Text © A.I. Markosyan, K.K. Hayrapetyan, S.H. Gabrielyan, V.Z. Shirinyan, S.S. Mamyan, J.A. Avakimyan, G.M. Stepanyan, 2018, published in Zhurnal Organicheskoi Khimii, 2018, Vol. 54, No. 4, pp. 604–611.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Markosyan, A.I., Hayrapetyan, K.K., Gabrielyan, S.H. et al. Some Transformations of 2-(Chloromethyl)-5,5-dimethyl-5,6-dihydrobenzo[h]quinazolin-4(3H)-one. Russ J Org Chem 54, 606–613 (2018). https://doi.org/10.1134/S1070428018040152

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428018040152

Search

Navigation