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Stepwise, Tandem, and One-Pot Syntheses of N-Aryl-2-(4-oxo-3,4-dihydroquinazolin-2-yl)benzamides in Water: A Green Protocol

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Abstract

Environmentally benign one-pot three-component synthesis of N-aryl-2-(4-oxo-3,4-dihydroquinazo­lin-2-yl)benzamides has been developed via the reaction of phthaloyl chloride with anilines and anthranilamide in water without any catalyst. The reaction involves easy workup, provides excellent yields, and utilizes water as solvent, which makes the proposed protocol green.

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REFERENCES

  1. Istvan, T.H. and Paul, T.A., Chem. Rev., 2007, vol. 107, p. 2167. https://doi.org

    Article  Google Scholar 

  2. Horvath, T.I., Chem. Rev., 2002, vol. 35, p. 685. https://doi.org/10.1021/ar020160a

    Article  CAS  Google Scholar 

  3. Lindström, U.K., Chem. Rev., 2002, vol. 102, p. 2751. https://doi.org/10.1021/cr010122p

    Article  CAS  PubMed  Google Scholar 

  4. Li, C.J., Chem. Rev., 2005, vol. 105, p. 3095. https://doi.org/10.1021/cr030009u

    Article  CAS  PubMed  Google Scholar 

  5. Li, C.J., Chem. Rev.,1993, vol. 93, p. 2023. https://doi.org/10.1021/cr00022a004

  6. Li, C.J. and Chen, L., Chem. Soc. Rev., 2006, vol. 35, p. 68. https://doi.org/10.1039/B507207G

    Article  PubMed  Google Scholar 

  7. Dallinger, D. and Kappe, C.O., Chem. Rev., 2007, vol. 107, p. 2563. https://doi.org/10.1021/cr0509410

    Article  CAS  PubMed  Google Scholar 

  8. Chanda, A. and Fokin, V.V., Chem. Rev., 2009, vol. 109, p. 725. https://doi.org/10.1021/cr800448q

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  9. Klijn, J.E. and Engberts, B.F.N., Nature, 2005, vol. 435, p. 746. https://doi.org/10.1038/435746a

    Article  CAS  PubMed  Google Scholar 

  10. Narayan, S., Muldoon, J., Finn, M.G., Fokin, V.V., Kolb, H.C., and Sharpless, K.B., Angew. Chem., Int. Ed., 2005, vol. 44, p. 3275. https://doi.org/10.1002/anie.200462883

    Article  CAS  Google Scholar 

  11. Rideout, DC. and Breslow, R., J. Am. Chem. Soc., 1980, vol. 102, p. 7816. https://doi.org/10.1021/ja00546a048

    Article  CAS  Google Scholar 

  12. Matloubi, M.F., Hojabri, L., Taheri, S., and Pirani, P., J. Iran. Chem. Soc., 2010, vol. 7, p. 781. https://doi.org/10.1007/BF03246069

    Article  Google Scholar 

  13. Liu, X.Y. and Che, C.M., Angew. Chem., Int. Ed., 2008, vol. 47, p. 3805. https://doi.org/10.1002/anie.200800160

    Article  CAS  Google Scholar 

  14. Herrer, C.I., Yao, X., Li, Z., and Li, CJ., Chem. Rev., 2007, vol. 107, p. 2546. https://doi.org/10.1021/cr050980b

    Article  CAS  Google Scholar 

  15. Zhou, F. and Li, C.J., Nat. Commun., 2014, vol. 5, p. 4254. https://doi.org/10.1038/ncomms5254

    Article  CAS  PubMed  Google Scholar 

  16. Tamaoki, T., Nomoto, H., Takahishi, I., Kato, Y., Morimoto, M., and Tomita, F., Biochem. Biophys. Res. Commun., 1986, vol. 135, p. 397. https://doi.org/10.1016/0006-291x(86)90008-2

    Article  CAS  PubMed  Google Scholar 

  17. Montalbetti, M., Cristian, A.G.N., and Falque, V., Tetrahedron, 2005, vol. 61, p. 10827. https://doi.org/10.1016/j.tet.2005.08.031

    Article  CAS  Google Scholar 

  18. Ghose, A.K., Viswanadhan, V.N., and Wendoloski, J.A., J. Comb. Chem., 1999, vol. 1, p. 55. https://doi.org/10.1021/cc9800071

    Article  CAS  PubMed  Google Scholar 

  19. Sirisoma, N., Pervin, A., Drewe, J., Tseng, B., and Cai, S.X., Bioorg. Med. Chem. Lett., 2009, vol. 19, p. 2710. https://doi.org/10.1016/j.bmcl.2009.03.121

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  20. Burbuliene, M.M., Jakubkiene, V., Mekuskiene, G., Udrenaite, P., Smicius, P., and Vainilavicius, P., Il Farmaco, 2004, vol. 59, p. 767. https://doi.org/10.1016/j.farmac.2004.05.007

    Article  CAS  PubMed  Google Scholar 

  21. Alagarasamy, M., Shankar, D., and Solomon, V.R., Arkivoc, 2006, vol. 2006, part (xvi), p. 149. https://doi.org/10.3998/ark.5550190.0007.g16

    Article  Google Scholar 

  22. Ozaki, K., Yamada, Y., Onine, T., Ishizuka, T., and Iwasawa, Y., J. Med. Chem., 1985, vol. 28, p. 568. https://doi.org/10.1021/jm50001a006

    Article  CAS  PubMed  Google Scholar 

  23. Sirisoma, N., Pervin, A., Zhang, H., Jiang, S., Willard­sen, J.A., Anderson, M.B., Mather, G., Pleiman, C.M., Kasibhatla, S., Tseng, B., Drewe, J., and Cai, S.X., J. Med. Chem., 2009, vol. 52, p. 2341. https://doi.org/10.1021/jm801315b

    Article  CAS  PubMed  Google Scholar 

  24. Antunes, R., Batista, H., Srivastava, R.M., Thomas, G., and Araujo, C.C., Bioorg. Med. Chem. Lett., 1998, vol. 8, p. 3071. https://doi.org/10.1016/S0960-894X(98)00558-7

    Article  CAS  PubMed  Google Scholar 

  25. Kumar, P.P., Reddy, Y.D., Reddy, Ch.V.R., Devi, B.R., and Dubey, P.K., Tetrahedron Lett., 2014, vol. 55, p. 2177. https://doi.org/10.1016/j.tetlet.2014.02.020

    Article  CAS  Google Scholar 

  26. Reddy, Y.D., Reddy, Ch.V.R., and Dubey, P.K., RSC Adv., 2014, vol. 4, p. 2974. https://doi.org/10.1039/C3RA44423F

    Article  CAS  Google Scholar 

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ACKNOWLEDGMENTS

The authors thank Jawaharlal Nehru Technological University (Hyderabad, India) for providing necessary facilities to carry out this work. B.S.N. is grateful to the Department of Science and Technology (Government of India, New Delhi) for financial support in the form of INSPIRE Fellowship.

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Authors and Affiliations

  1. Jawaharlal Nehru Technological University Hyderabad, Kukatpally, 500085, Hyderabad, India

    B. S. Narayana & Ch. V. R. Reddy

  2. Sreenidhi Institute of Science and Technology (Autonomous) Yamnampet, Ghatkesar, 501301, Hyderabad, India

    E. Laxminarayana

Authors
  1. B. S. Narayana
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  2. Ch. V. R. Reddy
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  3. E. Laxminarayana
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Correspondence to Ch. V. R. Reddy.

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Narayana, B.S., Reddy, C.V.R. & Laxminarayana, E. Stepwise, Tandem, and One-Pot Syntheses of N-Aryl-2-(4-oxo-3,4-dihydroquinazolin-2-yl)benzamides in Water: A Green Protocol. Russ J Org Chem 59, 465–469 (2023). https://doi.org/10.1134/S1070428023030144

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