Abstract
A green and eco-friendly synthesis of novel 2-(1H-indol-3-yl)-3-phenyl-2,3-dihydroquinazolin-4(1H)-one derivatives have been developed using L-proline as a simple catalyst. Two efficient methods have been described for the synthesis of dihydroquinazolin-4(1H)-one derivatives. In the first method, 1H-1,3-benzoxazine-2,4-dione reacted with substituted anilines and 1H-indole-3-carbaldehydes in water in the presence of L-proline as a catalyst, whereas in the second method, a similar reaction using 1H-indol-3-ylmethanol instead of indole-3-carbaldehyde was catalyzed by L-proline/K2CO3 at room temperature for 30 min to afford the same products. These two protocols involve eco-friendly and inexpensive catalysts and produce the target products in excellent yields with a sufficient purity, so that there was no need of column chromatography for their isolation or purification.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
REFERENCES
Gupta, P. and Mahajan, A., RSC Adv., 2015, vol. 5, p. 26686. https://doi.org/10.1039/C5RA00358J
Otto, S. and Engberts, J.B.F.N., Org. Biomol. Chem., 2003, vol. 1, p. 2809. https://doi.org/10.1039/B305672D
Ashis Kumar, N., Subarna, G., and Chakraborty, R., Molecules, 2007, vol. 12, p. 2413. https://doi.org/10.3390/12102413
Pathak, S.R., Malhotra, V., and Shanker, R.N., Cent. Nerv. Syst. Agents Med. Chem., 2014, vol. 14, p. 34. https://doi.org/10.2174/1871524914666140825144729
Jangam, S.S. and Wankhede, S.B., Russ. J. Gen. Chem., 2019, vol. 89, p. 1029. https://doi.org/10.1134/S1070363219050256
Yadav, M.R., Shirude, S.T., Parmar, A., Balaraman, R., and Giridhar, R., Chem. Heterocycl. Compd., 2006, vol. 42, p. 1038. https://doi.org/10.1007/s10593-006-0201-4
Zayed, M.F. and Hassan, M.H., Saudi Pharm. J., 2014, vol. 22, p. 157. https://doi.org/10.1016/j.jsps.2013.03.004
El Azab, A.S. and El Tahir, K.E.H., Bioorg. Med. Chem. Lett., 2012, vol. 22, p. 327. https://doi.org/10.1016/j.bmcl.2011.11.007
Cantarelli, G., Farmaco, Ed. Sci., 1970, vol. 25, p. 761. PMID: 5484777
Mhaske, S.B. and Argade, N.P., Tetrahedron, 2006, vol. 62, p. 9787. https://doi.org/10.1016/j.tet.2006.07.098
Weber, L., Drug Discovery Today, 2002, vol. 7, p. 143. https://doi.org/10.1016/s1359-6446(01)02090-6
Sunderhaus, J.D., Dockendorff, C., and Martin, S.F., Org. Lett., 2007, vol. 9, p. 4223. https://doi.org/10.1021/ol7018357
Preeti and Singh, K.N., Org. Biomol. Chem., 2018, vol. 16, p. 9084. https://doi.org/10.1039/C8OB01872C
Cioc, R.C., Ruijter, E., and Orru, R.V.A., Green Chem., 2014, vol. 16, p. 2958. https://doi.org/10.1039/C4GC00013G
Biggs-Houck, J.E., Younai, A., and Shaw, J.T., Curr. Opin. Chem. Eng., 2010, vol. 14, p. 371. https://doi.org/10.1016/j.cbpa.2010.03.003
ACKNOWLEDGMENTS
The authors are grateful to the management of Dr. Reddy’s Laboratories Ltd. for supporting this work and highly appreciate the co-operation from all the supporting function colleagues.
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
The authors declare the absence of conflict of interest.
Rights and permissions
About this article
Cite this article
Hari Krishna Reddy, V., Prashanth Reddy, G., Krishna Mohan, T. et al. L-Proline/K2CO3-Catalyzed Eco-friendly Synthesis of Novel 2-(1H-Indol-3-yl)-3-phenyl-2,3-dihydroquinazolin-4(1H)-one Derivatives. Russ J Org Chem 57, 1678–1684 (2021). https://doi.org/10.1134/S1070428021100171
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070428021100171