Skip to main content
SpringerLink
Log in

A Metal- and Ligand-Free Synthesis of Quinazolin-4(3H)-ones via a Bu4NI/TBHP-Mediated Oxidative Cleavage of the Olefinic C=C Bond

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

Abstract

A metal and ligand-free protocol has been developed for the synthesis of quinazolin-4(3H)-ones in moderate to good yields from o-aminobenzamide and alkenes via a Bu4NI/TBHP-mediated oxidative cleavage of the C=C bond in alkenes.

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
Scheme
Scheme

Similar content being viewed by others

REFERENCES

  1. Michael, J.P., Nat. Prod. Rep., 2005, vol. 22, p. 627. https://doi.org/10.1039/B413750G

    Article  CAS  PubMed  Google Scholar 

  2. Michael, J.P., Nat. Prod. Rep., 2004, vol. 21, p. 650. https://doi.org/10.1039/B310691H

    Article  CAS  PubMed  Google Scholar 

  3. Michael, J.P., Nat. Prod. Rep., 2003, vol. 20, p. 476. https://doi.org/10.1039/B208140G

    Article  CAS  PubMed  Google Scholar 

  4. Mhaske, S.B. and Argade, N.P., Tetrahedron, 2006, vol. 62, p. 9787. https://doi.org/10.1016/j.tet.2006.07.098

    Article  CAS  Google Scholar 

  5. Connolly, D.J., Cusack, D., O’Sullivan, T.P., and Guiry, P.J., Tetrahedron, 2005, vol. 61, p. 10153. https://doi.org/10.1016/j.tet.2005.07.010

    Article  CAS  Google Scholar 

  6. Ge, W.L., Zhu, X., and Wei, Y., RSC Adv., 2013, vol. 3, p. 10817. https://doi.org/10.1039/C3RA40872H

    Article  CAS  Google Scholar 

  7. Yoshida, S., Aoyagi, T., Harada, S., Matsuda, N., Ikeda, T., Naganawa, H., Hamada, M., and Takeuchi, T., J. Antibiot., 1991, vol. 44, p. 111. https://doi.org/10.7164/antibiotics.44.111

    Article  CAS  PubMed  Google Scholar 

  8. Ma, Z.Z., Hano, Y., Nomura, T., and Chen, Y., J. Heterocycles, 1997, vol. 46, p. 541. https://doi.org/10.3987/COM-97-S65

    Article  CAS  Google Scholar 

  9. Nanda, A.K., Ganguli, S., and Chakraborty, R., Molecules, 2007, vol. 12, p. 2413. https://doi.org/10.3390/12102413

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  10. Aly, M.M., Mohamed, Y.A., El-Bayouki, K.A., Basyouni, W.M., and Abbas, S.Y., Eur. J. Med. Chem., 2010, vol. 45, p. 3365. https://doi.org/10.1016/j.ejmech.2010.04.020

    Article  CAS  PubMed  Google Scholar 

  11. Ma, Z., Hano, Y., and Nomura, T., Heterocycles, 2005, vol. 65, p. 2203. https://doi.org/10.3987/REV-05-599

    Article  CAS  Google Scholar 

  12. Kung, P.P., Casper, M.D., Cook, K.L., Wilson Lingard, L., Risen, L.M., Vickers, T.A., Ranken, R., Blyn, L.B., Wyatt, R., Cook, P.D., and Ecker, D., J. Med. Chem., 1999, vol. 42, p. 4705. https://doi.org/10.1021/jm9903500

    Article  CAS  PubMed  Google Scholar 

  13. Malamas, M.S. and Millen, J., J. Med. Chem., 1991, vol. 34, p. 1492. https://doi.org/10.1021/jm00108a038

    Article  CAS  PubMed  Google Scholar 

  14. De Laszlo, S.E., Quagliato, C.S., Greenlee, W.J., Patchett, A.A., Lotti, V.J., Chen, T.B., Scheck, S.A., and Faust, A., J. Med. Chem., 1993, vol. 36, p. 3207. https://doi.org/10.1021/jm00073a024

    Article  CAS  PubMed  Google Scholar 

  15. Kikuchi, H., Yamamoto, K., Horoiwa, S., Hirai, S., Kasahara, R., Hariguchi, N., Matsumoto, M., and Oshima, Y., J. Med. Chem., 2006, vol. 49, p. 4698. https://doi.org/10.1021/jm0601809

    Article  CAS  PubMed  Google Scholar 

  16. Malecki, N., Carato, P., and Rigo, B., Bioorg. Med. Chem., 2004, vol. 12, p. 641 https://doi.org/10.1016/j.bmc.2003.10.014

    Article  CAS  PubMed  Google Scholar 

  17. Kenichi, O., Yoshihisa, Y., Toyonari, O., Toru, I., and Yoshio, I., J. Med. Chem., 1985, vol. 28, p. 568. https://doi.org/10.1021/jm50001a006

    Article  Google Scholar 

  18. Hour, M.J., Huang, L.J., Kuo, S.C., Xia, Y., Bastow, K., Nakanishi, Y., Hamel, E., and Lee, K.H., J. Med. Chem., 2000, vol. 43, p. 4479. https://doi.org/10.1021/jm000151c

    Article  CAS  PubMed  Google Scholar 

  19. Purcell, J.W., Davis, J., Reddy, M., Shamra, M., Kimberly, S., Vo, H., Thomsen, K., Bean, P., Kuo, W.L., Ziyad, S., Billig, J., Feiler, H.S., Gray, J.W., Wood, K.W., and Cases, S., Clin. Cancer Res., 2010, vol. 16, p. 566. https://doi.org/10.1158/1078-0432.CCR-09-1498

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  20. Inoue, I., Oine, T., Yamada, Y., Tani, J., lshida, R., and Ochiai, T., US Patent no. 3966731, 1974.

  21. Rajendra, S.R. and Umesh, A.K., Synthesis, 2016, vol. 48, p. 1253. https://doi.org/10.1055/s-0035-1560413

    Article  CAS  Google Scholar 

  22. Upadhyaya, K., Thakur, R.K., Shukla, S.K., and Tripathi, R.P., J. Org. Chem., 2016, vol. 81, p. 5046. https://doi.org/10.1021/acs.joc.6b00599

    Article  CAS  PubMed  Google Scholar 

  23. Laclef, S., Harari, M., Godeau, J., Schmitz-Afonso, I., Bischoff, L., Hoarau, C., Levacher, V., Fruit, C., and Besson, T., Org. Lett., 2015, vol. 17, p. 1700. https://doi.org/10.1021/acs.orglett.5b00467

    Article  CAS  PubMed  Google Scholar 

  24. Feng, L., Lei, L., and Juan, M., Org. Chem. Front., 2015, vol. 2, p. 1589. https://doi.org/10.1039/C5QO00255A

    Article  CAS  Google Scholar 

  25. Zibin, L., Li-Yan, Z., Chao, L., Fubiao, Y., Fensheng, Q., Shuwen, L., and Baomin, X., Molecules, 2018, p. 23, p. 1. https://doi.org/10.3390/molecules23092325

  26. Dan, Z., Teng, W., and Jian-Xin, L., Chem. Commun., 2014, vol. 50, p. 6471. https://doi.org/10.1039/C4CC02648A

    Article  Google Scholar 

  27. Bie, Z., Li, G., Wang, L., Lv, Y., Niu, J., and Gao, S., Tetrahedron Lett., 2016, vol. 57, p. 4935. https://doi.org/10.1016/j.tetlet.2016.09.077

    Article  CAS  Google Scholar 

  28. Ying-Hui, S., Li-Yan, F., Xiang-Xiong, Li., and Meng-Xia, L., Chin. Chem. Lett., 2015, vol. 26, p. 1355. https://doi.org/10.1016/j.cclet.2015.07.026

    Article  CAS  Google Scholar 

  29. Yuko, M., Sayaka, I., Takashi, M., Tsuyoshi, N., Nagaaki, S., and Shigeru, T., Bioorg. Med. Chem. Lett., 2009, vol. 19, p. 4075. https://doi.org/10.1016/j.bmcl.2009.06.025

    Article  CAS  Google Scholar 

  30. Chu, M., Xiang-Guang, M., Xiao-Hong, L., and Xiao, P., RSC Adv., 2015, vol. 5, p. 69487. https://doi.org/10.1039/C5RA14093E

    Article  CAS  Google Scholar 

  31. Wei, L., Wu, G., Wenxia, G., Jinchang, D., Xiaobo, H., Miaochang, L., and Huayue, W., Org. Chem. Front., 2018, vol. 5, p. 2734. https://doi.org/10.1039/C8QO00670A

    Article  CAS  Google Scholar 

  32. Teng, Q.H., Sun, Y., Yao, Y., Tang, H.T., Li, J.R., and Pan, Y.M., ChemElectroChem, 2019, vol. 6, p. 3120. https://doi.org/10.1002/celc.201900682

    Article  CAS  Google Scholar 

  33. Abdullaha, M., Mohammed, S., Ali, M., Kumar, A., Vishwakarma, R.A., and Bharate, S.B., J. Org. Chem., 2019, vol. 84, p. 5129. https://doi.org/10.1021/acs.joc.9b00138

    Article  CAS  PubMed  Google Scholar 

  34. Wu, X.F., Gong, J.L., and Qi, X., Org. Biomol. Chem., 2014, vol. 12, p. 5807. https://doi.org/10.1039/c4ob00276h

    Article  CAS  PubMed  Google Scholar 

  35. Habtamu, A., Siddaiah, V., and Venkateswara Rao, B., RSC Adv., 2016, vol. 6, p. 82289. https://doi.org/10.1039/c6ra18968g

    Article  CAS  Google Scholar 

  36. Habtamu, A., Siddaiah, V., and Venkateswara Rao, B., ChemistrySelect, 2017, vol. 2, p. 4165. https://doi.org/10.1002/slct.201700241

    Article  CAS  Google Scholar 

  37. Ganesh, M., Srimanta, G., Saroj, K.R., Ahalya, B., and Bhisma, K.P., Chem. Commun., 2014, vol. 50, p. 12193. https://doi.org/10.1039/c4cc05050a

    Article  Google Scholar 

Download references

ACKNOWLEDGMENTS

The authors are grateful to DAE-BRNS, Mumbai for financial assistance [project no. 37(2)/14/02/2014-BRNS]. Mr Bharat Kumar acknowledges the University Grants Commission for financial support through the Rajiv Gandhi National Fellowship (project no. RGNF-2015-17-SC-AND-14252).

Author information

Authors and Affiliations

  1. Department of Organic Chemistry and FDW, Andhra University, 530003, Visakhapatnam, India

    B. K. Karasala, P. Gollamudi, B. Inkollu & S. Vidavalur

Authors
  1. B. K. Karasala
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. P. Gollamudi
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. B. Inkollu
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. S. Vidavalur
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to S. Vidavalur.

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

Karasala, B.K., Gollamudi, P., Inkollu, B. et al. A Metal- and Ligand-Free Synthesis of Quinazolin-4(3H)-ones via a Bu4NI/TBHP-Mediated Oxidative Cleavage of the Olefinic C=C Bond. Russ J Org Chem 56, 1446–1454 (2020). https://doi.org/10.1134/S1070428020080163

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428020080163

Keywords:

Search

Navigation