Skip to main content
Log in

Palladium-Catalyzed Synthesis of 4-Aminoquinazolines from Amide Oxime Ethers and 2-Iodobenzonitrile

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

Abstract

4-Substituted O-benzyl benzamide oximes reacted with 2-iodobenzonitrile in the presence of 0.1 mol % of [Pd2(dba)3], 0.2 mol % of XantPhos, and 1.5 equiv of Cs2CO3 in dioxane under argon to give 2-arylquinazolin-4-amines. The described reaction is a new type of cascade processes, which affords 4-amino-quinazoline derivatives without using highly reactive chlorinating agents.

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.

Similar content being viewed by others

References

  1. Lipunova, G.N., Nosova, E.V., Charushin, V.N., and Chupakhin, O.N., Russ. Chem. Rev., 2016, vol. 85, no. 7, p. 759. doi https://doi.org/10.1070/rcr4591

    Article  CAS  Google Scholar 

  2. Mphahlele, M.J., Maluleka, M.M., Aro, A., McGaw, L.J., and Choong, Y.S., J. Enzyme Inhib. Med. Chem., 2018, vol. 33, no. 1, p. 1516. doi https://doi.org/10.1080/14756366.2018.1510919

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  3. Liu, F., Huai, Z., Xia, G., Song, L., Li, S., Xu, Y., Hong, K., Yao, M., Liu, G., and Huang, Y., Bioorg. Med. Chem. Lett., 2018, vol. 28, no. 14, p. 2561. doi https://doi.org/10.1016/j.bmcl.2018.05.033

    Article  CAS  PubMed  Google Scholar 

  4. Fan, Y.H., Ding, H.W., Liu, D.D., Song, H.R., Xu, Y.N., and Wang, J., Bioorg. Med. Chem., 2018, vol. 26, no. 8, p. 1675. doi https://doi.org/10.1016/j.bmc.2018.02.015

    Article  CAS  PubMed  Google Scholar 

  5. Hao, C., Zhao, F., Song, H., Guo, J., Li, X., Jiang, X., Huan, R., Song, S., Zhang, Q., Wang, R., Wang, K., Pang, Y., Liu, T., Lu, T., Huang, W., Wang, J., Lin, B., He, Z., Li, H., Li, F., Zhao, D., and Cheng, M., J. Med. Chem., 2018, vol. 61, no. 1, p. 265. doi https://doi.org/10.1021/acs.jmedchem.7b01342

    Article  CAS  PubMed  Google Scholar 

  6. Feng, J.B. and Wu, X.F., Org. Biomol. Chem., 2015, vol. 13, no. 43, p. 10656. doi https://doi.org/10.1039/c5ob01587a

    Article  CAS  PubMed  Google Scholar 

  7. Yan, S., Dong, Y., Peng, Q., Fan, Y., Zhang, J., and Lin, J.-B., RSC Adv., 2013, vol. 3,5563. doi https://doi.org/10.1039/c3ra23059g

    CAS  Google Scholar 

  8. Qiao, R., Fu, H., Yang, X., Liu, H., Jiang, Y., and Zhao, Y., Synlett, 2010, vol. 2010,101. doi https://doi.org/10.1055/s-0029-1218530

    Article  CAS  Google Scholar 

  9. Chen, D., Yang, L., Luo, H., Sun, Y., Shi, Z., Ni, K., and Li, F., Synthesis, 2017, vol. 49, no. 11, p. 2535. doi https://doi.org/10.1055/s-0036-1588727

    Article  CAS  Google Scholar 

  10. Jia, F.C., Zhou, Z.W., Xu, C., Cai, Q., Li, D.K., and Wu, A.X., Org. Lett., 2015, vol. 17, no. 17, p. 4236. doi https://doi.org/10.1021/acs.orglett.5b02020

    Article  CAS  PubMed  Google Scholar 

  11. Bolotin, D.S., Bokach, N.A., Demakova, M.Ya., and Kukushkin, V.Yu., Chem. Rev., 2017, vol. 117, no. 21, p. 13039. doi https://doi.org/10.1021/acs.chemrev.7b00264

    Article  CAS  PubMed  Google Scholar 

  12. Patil, S.S., Mhaske, P.C., Patil, S.V., and Bobade, V.D., J. Heterocycl. Chem., 2011, vol. 48, no. 3, p. 652. doi https://doi.org/10.1002/jhet.572

    Article  CAS  Google Scholar 

  13. Bolotin, D.S., Bokach, N.A., and Kukushkin, V.Yu., Coord. Chem. Rev., 2016, vol. 313,62. doi https://doi.org/10.1016/j.ccr.2015.10.005

    Article  CAS  Google Scholar 

  14. Dondoni, A., J. Chem. Soc., Chem. Commun., 1975, no. 18, p. 761. doi https://doi.org/10.1039/C39750000761

    Google Scholar 

  15. Akazome, M., Kondo, T., and Watanabe, Y., J. Mol. Catal., 1993, vol. 80, no. 3, p. 383. doi https://doi.org/10.1016/0304-5102(93)85011-H

    Article  CAS  Google Scholar 

  16. Mahajan, U.S., Godinde, R.R., and Mandhare, P.N., Synth. Commun., 2011, vol. 41,2195. doi https://doi.org/10.1080/00397911.2010.488307

    Article  CAS  Google Scholar 

  17. Duros, V., Sartzi, H., Teat, S.J., Sanakis, Y., Roubeau, O., and Perlepes, S.P., Inorg. Chem. Commun., 2014, vol. 50,117. doi https://doi.org/10.1016/j.inoche.2014.10.017

    Article  CAS  Google Scholar 

  18. Anbazhagan, M., Stephens, C.E., and Boykin, D.W., Tetrahedron Lett., 2002, vol. 43, no. 23, p. 4221. doi https://doi.org/10.1016/S0040-4039(02)00775-X

    Article  CAS  Google Scholar 

  19. Abele, E., Rubina, K., Golomba, L., and Abele, R., Heterocycl. Lett., 2012, vol. 2, no. 1, p. 85.

    CAS  Google Scholar 

  20. Xu, M.M., Cao, W.B., Xu, X.P., and Ji, S.J., Chem. Commun., 2018, vol. 54, no. 89, p. 12602. doi https://doi.org/10.1039/c8cc07721e

    Article  CAS  Google Scholar 

  21. Allen, F.H., Kennard, O., Watson, D.G., Brammer, L., Orpen, A.G., and Taylor, R., J. Chem. Soc., Perkin Trans., 1987, vol. 12, p. S1. doi https://doi.org/10.1039/P298700000S1

    Article  Google Scholar 

  22. Sheldrick, G.M., Acta Crystallogr., Sect. A, 2008, vol. 64,112. doi https://doi.org/10.1107/S0108767307043930

    Article  CAS  PubMed  Google Scholar 

  23. Dolomanov, O.V., Bourhis, L.J., Gildea, R.J., Howard, J.A.K., and Puschmann, H., J. Appl. Crystallogr., 2009, vol. 42, no. 2, p. 339. doi https://doi.org/10.1107/S0021889808042726

    Article  CAS  Google Scholar 

  24. CrysAlisPro. Data Collection and Processing Software for Agilent X-ray Diffractometers. 1.171.36.20, Agilent Technologies. 2012.

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to M. Ya. Demakova.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Demakova, M.Y., Islamova, R.M. & Suslonov, V.V. Palladium-Catalyzed Synthesis of 4-Aminoquinazolines from Amide Oxime Ethers and 2-Iodobenzonitrile. Russ J Gen Chem 89, 668–672 (2019). https://doi.org/10.1134/S1070363219040054

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070363219040054

Keywords

Navigation