Skip to main content
Log in

One-Pot Green Synthesis of 2-Amino-7,7-dimethyl-5-oxo-4-(1H-pyrazol-5-yl)-5,6,7,8-tetrahydro-4H-chromene-3-carbonitriles

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

Abstract

–The one-pot three-component combinatorial synthesis of pharmaceutically active 2-amino-7,7-dimethyl-5-oxo-4-(1H-pyrazol-5-yl)-5,6,7,8-tetrahydro-4H-chromene-3-carbonitriles or -carboxylates, which involves a DBU-catalyzed reaction of 1H-pyrazole-5-carbaldehyde, 5,5-dimethylcyclohexane-1,3-dione, and malononitrile or ethyl 2-cyanoacetate at 60–65°C in ethanol for 60–90 min. The procedure offers a few advantages, including versatility, good yields, facility, and environmentally friendly conditions.

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

Access this article

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

Instant access to the full article PDF.

Fig. 1.
Scheme

REFERENCES

  1. Karthikeyan, C., Malla, R., Ashby, C.R., Amawi, H., Abbott, K.L., Moore, J., Chen, J., Balch, C., Flannery, P.C., Trivedi, P., Lee, C., Faridi, J.S., Pondugula, S.R., and Tiwari, A.K., Cancer Lett., 2016, vol. 376, p. 118. https://doi.org/10.1016/j.canlet.2016.03.030

    Article  CAS  PubMed  Google Scholar 

  2. Karnakar, K., Narayana, S.M., Ramesh, K., Satish, G., Jagadeesh, B.N., and Nageswar, Y.V.D., Tetrahedron Lett., 2012, vol. 53, p. 2897. https://doi.org/10.1016/j.tetlet.2012.03.135

    Article  CAS  Google Scholar 

  3. Mohamed, L.W., Shaaban, M.A., Zaher, A.F., and Elsahar, A.M., Bioorg. Chem., 2019, vol. 83, p. 47. https://doi.org/10.1016/j.bioorg.2018.10.014

    Article  CAS  PubMed  Google Scholar 

  4. Singh, S.K., Rebby, P.G., Rao, K.S., Lohray, B.B., Misra, P., Rajjak, S.A., Rao, Y.K., and Venkateswarlu, A., Bioorg. Med. Chem. Lett., 2004, vol. 14, p. 499. https://doi.org/10.1016/j.tetlet.2012.03.135

    Article  CAS  PubMed  Google Scholar 

  5. Safaei, G.J., Sadeghzadeh, R., and Shahbazi, A.H., RSC Adv., 2016, vol. 6, p. 33676. https://doi.org/10.1039/C6RA02906J

    Article  ADS  CAS  Google Scholar 

  6. Paul, S., and Das, A.R., Tetrahedron Lett., 2013, vol. 54, p. 1149. https://doi.org/10.1016/j.tetlet.2012.12.079

    Article  CAS  Google Scholar 

  7. Maddila, S.N., Maddila, S., Khumalo, M., Bhaskaruni, S.V.H.S., and Sreekantha, B.J., J. Mol. Struct., 2019, vol. 1185, p. 357. https://doi.org/10.1016/j.molstruc.2019.03.006

    Article  ADS  CAS  Google Scholar 

  8. Maddila, S., Gangu, K.K., Maddila, S.N., and Jonnalagadda, S.B., Mol. Divers., 2017, vol. 21, p. 247. https://doi.org/10.2174/1570179414666161208164731

    Article  CAS  PubMed  Google Scholar 

  9. Rambhau, P.G., and Ambarsing, P.R., Drug Invent. Today, 2013, vol. 5, p. 148. https://doi.org/10.1016/j.dit.2013.05.010

    Article  CAS  Google Scholar 

  10. Maram, K., and Raju, R.R., Russ. J. Org. Chem., 2022, vol. 58, p. 1030. https://doi.org/10.1134/S1070428022070132

    Article  CAS  Google Scholar 

  11. Khurana, J.M., Chaudhary, A., Nand, B., and Lumb, A., Tetrahedron Lett., 2012, vol. 53, p. 3018. https://doi.org/10.1016/j.tetlet.2012.04.001

    Article  CAS  Google Scholar 

  12. Ramesh, V., Purna, P.C.R., Ramachandran, D., and Kalyan, A.C., Eur. Chem. Bull., 2019, vol. 8, p. 318. https://doi.org/10.17628/ecb.2019.8.318-321

    Article  CAS  Google Scholar 

  13. Sheldon, R.A., Chem. Commun., 2001, p. 2399. https://doi.org/10.1039/B107270F

  14. Toda, F., and Tanaka, K., Chem. Rev., 2000, vol. 100, p. 1025. https://doi.org/10.1021/cr940089p

    Article  CAS  PubMed  Google Scholar 

  15. Luo, Z.Y., Zang, Q.S., Oderaotoshi, Y., and Curran, D.P., Science, 2001, vol. 291, p. 1766. https://doi.org/10.1126/science.1057567

    Article  ADS  CAS  PubMed  Google Scholar 

  16. Temple, C., Rose, J.D., Comber, R.N., and Rener, G.A., J. Med. Chem., 1987, vol. 30, p. 1746. https://doi.org/10.1021/jm00393a011

    Article  CAS  PubMed  Google Scholar 

  17. Kehinde, I., Ramharack, P., Nlooto, M., and Gordon, M., Heliyon, 2019, vol. 5, p. e02565. https://doi.org/10.1016/j.heliyon.2019.e02565

Download references

Funding

This work was supported by ongoing institutional funding. No additional grants to carry out or direct this particular research were obtained.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to R. Ramesh Raju.

Ethics declarations

The authors of this work declare that they have no conflicts of interest.

Additional information

Publisher’s Note. Pleiades Publishing remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Supplementary information

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Maram, K., Anitha, K., Sreenivasulu, R. et al. One-Pot Green Synthesis of 2-Amino-7,7-dimethyl-5-oxo-4-(1H-pyrazol-5-yl)-5,6,7,8-tetrahydro-4H-chromene-3-carbonitriles. Russ J Org Chem 59, 1982–1987 (2023). https://doi.org/10.1134/S1070428023110179

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428023110179

Keywords:

Navigation