Abstract
A simple, efficient, and green protocol has been developed for the synthesis of 2-amino-4-aryl-4H-chromene-3-carbonitriles via a one-pot three-component condensation of resorcinol, malononitrile, and substituted aromatic aldehydes in ethanol under reflux using InCl3 as a catalyst. This methodology has a number of advantages such as the use of a very small amount of catalyst, easy access, short reaction time, easy workup, high yields, and nontoxicity of the catalyst and solvent.
Similar content being viewed by others
REFERENCES
Dongamanti, A., Bommidi, V.L., Sidda, R., Arram, G., and Shaik, A., Chem. Heterocycl. Compd., 2015, vol. 51, p. 462. https://doi.org/10.1007/s10593-015-1719-0
Cinzia, C., Luca, P.M., and Nicoletta, D., Bioorg. Med. Chem., 2014, vol. 22, p. 1201. https://doi.org/10.1016/j.bmc.2013.11.054
Tilak Raj, R.K., Bhatia, A.M., Sharma, A.K., and Saxena, M.P., Eur. J. Med. Chem., 2010, vol. 45, p. 790. https://doi.org/10.1016/j.ejmech.2009.11.001
Gourdeau, H., Leblond, L., Hamelin, B., Desputeau, C., Dong, K., Kianicka, I., Custeau, D., Boudreau, C., Geerts, L., Cai, S.-X., Drewe, J., Labrecque, D., Kasibhatla, S., and Tseng, B., Mol Cancer Ther., 2004, vol. 3 p. 1375. https://doi.org/10.1158/1535-7163.1375.3.11
Mashooq, A.B., Nadeem, S., and Suroor, A.K., Acta Pol. Pharm., 2008, vol. 65, p. 235. PMID 18666431
Ebtisam, A.A.H., Mohamed, H.E., Amel, G.A.E., and Fathy Mohamed A.A.T. Heterocycles, 1987, vol. 26, p. 903. https://doi.org/10.3987/R-1987-04-0903
Magar, R.L., Thorat, P.B., Jadhav, V.B., Tekale, S.U., Dake, S.A., Patil, B.R., and Pawar, R.P., J. Mol. Catal. A: Chem., 2013, vol. 374, p. 118. https://doi.org/10.1016/j.molcata.2013.03.022
Javad, S., Marzieh, H., and Zohre, Z., Arab. J. Chem., 2017, vol. 10, p. 2994. https://doi.org/10.1016/j.arabjc.2013.11.038
Sedaghat, M.E., Rajabpour, M.B., Nazarifar, M.R., and Farhadi, F., Appl. Clay Sci., 2014, vol. 95, p. 55. https://doi.org/10.1016/j.clay.2014.02.016
Bagher, A., Mohammad, S., and Mehdi, A., Res. Chem. Intermed., 2016, vol. 42, p. 3413. https://doi.org/10.1007/s11164-015-2220-1
Elagamey, A.G.A., El-Taweel, F.M.A., Khodeir, M.N.M., and Elnagdi, M.H., Bull. Chem. Soc. Jpn., 1993, vol. 66, p. 464. https://doi.org/10.1246/bcsj.66.464
Mandar, P.S., Siddheshwar, K., and Shriniwas, D.S., Tetrahedron Lett., 2009, p. 719. https://doi.org/10.1016/j.tetlet.2008.11.114
Elinson, M.N., Ilovaisky, A.I., Merkulova, V.M., Belyakov, P.A., Chizhov, A.O., and Nikishin, G.I., Tetrahedron, 2010, vol. 66, p. 4043. https://doi.org/10.1016/j.tet.2010.04.024
Kai, G., Hua-Lan, W., and Dong-Fang, Z.L., Catal. Commun., 2008, vol. 9, p. 650. https://doi.org/10.1016/j.catcom.2007.07.010
ACKNOWLEDGMENTS
The authors are grateful to Principal, Yeshwant Mahavidyalaya, Nanded, for providing laboratory facilities, UGC, New Delhi (File no.41-230/2012) (SR) for financial support, and The Director, Punjab University, Chandigarh for providing spectra.
Author information
Authors and Affiliations
Corresponding authors
Ethics declarations
The authors declare the absence of conflict of interest.
Rights and permissions
About this article
Cite this article
Choudhare, S.S., Bhosale, V.N. & Chopade, M. Synthesis of 2-Amino-4H-chromene Derivatives Using InCl3 and Their Antimicrobial Evaluation. Russ J Org Chem 58, 913–916 (2022). https://doi.org/10.1134/S1070428022060227
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070428022060227