Skip to main content
SpringerLink
Log in

Synthesis of Novel Spiro[chromene-4,3'-indolines] and Spiro(indoline-3,4'-pyrano[3,2-h]quinolines)

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

Abstract

The condensation of 1-alkylisatines with malononitrile and 8-hydroxyquinoline or 5,5-dimethyl-cyclohexane-1,3-dione in the presence of an aqueous solution of trimethylamine proceeds regioselectively as a one-pot three-component domino process to form spiro[chromene-4,3'-indoline] and spiro(indoline-3,4'-pyrano[3,2-h]quinoline).

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. Ziarani, G.M., Moradi, R., and Lashgari, N., Arkivoc, 2016, vol. i, p. 1. https://doi.org/10.3998/ark.5550190.p009.385

  2. Heravi, M.M., Zakeri, M., and Moharami, A., J. Chem.Sci., 2012, vol. 124, p. 865. https://doi.org/10.1007/s12039012-0284-7

    Article  CAS  Google Scholar 

  3. Esmaeili, A.A., Ghalandarabad, S.A., Mesbah, F., Tasmimi, M., Izadyar, M., Fakhari, A.R., and Salimi, A.R., Tetrahedron, 2015, vol. 71, p. 2458. https://doi.org/10.1016/j.tet.2015.01.055

    Article  CAS  Google Scholar 

  4. Ma, J. and Hecht, S.M., Chem. Commun., 2004, p. 1190. https://doi.org/10.1039/b402925a

  5. Galliford, C.V. and Scheidt, K.A., Angew. Chem. Int. Ed., 2007, vol. 46, p. 8748. https://doi.org/10.1002/anie.200701342

    Article  CAS  Google Scholar 

  6. Kidwai, M., Jain, A., Nemaysh, V., Kumar, R., and Luthra, P.M., Med. Chem. Res., 2013, vol. 22, p. 2717. https://doi.org/10.1007/s00044-012-0249-x

    Article  CAS  Google Scholar 

  7. Tian, Y., Nam, S., Liu, L., Yakushijin, F., Yakushijin, K., Buettner, R., Liang, W., Yang, F., Ma, Y., Horne, D., and Jove, R., PLoS ONE, 2012, vol. 7, e49306, p. 1. https://doi.org/10.1371/journal.pone.0049306

    Article  CAS  Google Scholar 

  8. Dandia, A., Singh, R., Khaturia, S., Merienne, C., Morgant, G., and Loupy, A., Bioorg. Med.Chem., 2006, vol. 14, p. 2409. https://doi.org/10.1016/j.bmc.2005.11.025

    Article  CAS  PubMed  Google Scholar 

  9. Khafagy, M.M., El-Wahab, A.H.F.A., Eid, F.A., and El-Agrody, A.M., Farmaco, 2002, vol. 57, p. 715. https://doi.org/10.1016/S0014-827X(02)01263-6

    Article  CAS  PubMed  Google Scholar 

  10. Pogosyan, S.A. Avakimyan, Dzh.A., and Stepanyan, G.M., Russ. J. Org. Chem., 2016, vol. 52, p. 1308. https://doi.org/10.1134/S1070428018120254

  11. Pogosyan, S.A. Paronikyan, R.V., Stepanyan, G.M., and Grigoryan, A.G., Khim. Zh. Arm., 2016, vol. 69, p. 518.

    Google Scholar 

  12. Wang, J., Li, J., Liu, H., Xu, Z., and Zhu, S., Lett. Org.Chem., 2015, vol. 12, p. 62. https://doi.org/10.2174/157017861201150112124526

    Article  CAS  Google Scholar 

  13. Zhao, H.W., Li, B., Tian, T., Meng, W., Yang, Z., Song, X.Q., Chen, X.Q., and Pang, H.L., Eur. J. Org. Chem., 2015, vol. 15, p. 3320. https://doi.org/10.1002/ejoc.201500152

    Article  CAS  Google Scholar 

  14. Ghahremanzadeh, R., Hosseini, G., Akbarzadeh, R., and Bazgir, A., J. Heterocycl. Chem., 2013, vol. 50, p. 272. https://doi.org/10.1002/jhet.1010

    Article  CAS  Google Scholar 

  15. Karamthulla, S., Pal, S., Khan, M.N., and Choudhury, L.H., RSC Adv., 2013, vol. 3, p. 15576. https://doi.org/10.1039/c3ra43289k

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Scientific and Technological Center of Organic and Pharmaceutical Chemistry, NAS of Armenia, 0019, Yerevan, Armenia

    S. A. Pogosyan & A. A. Harutyunyan

  2. University of Cologne, 50923, Cologne, Germany

    M. V. Pogosyan

  3. Armenian–Russian University, 0051, Yerevan, Armenia

    A. A. Harutyunyan

Authors
  1. S. A. Pogosyan
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. M. V. Pogosyan
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. A. Harutyunyan
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to S. A. Pogosyan.

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

Pogosyan, S.A., Pogosyan, M.V. & Harutyunyan, A.A. Synthesis of Novel Spiro[chromene-4,3'-indolines] and Spiro(indoline-3,4'-pyrano[3,2-h]quinolines). Russ J Org Chem 56, 213–217 (2020). https://doi.org/10.1134/S1070428020020062

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428020020062

Keywords:

Search

Navigation