Abstract
Ecofriendly, water mediated, one-pot three-component synthesis of novel 2-(5,6-dicyano-1H-benzo[d]imidazol-2-yl)-N-arylbenzamides have been developed by the reactions of phthalic anhydride with substituted anilines and 4,5-diaminophthalonitrile in water for 90–120 min at 100°C without any catalyst. The reactions involve easy workup, provide excellent yields, and use water as a green solvent.
REFERENCES
Istvan, T.H. and Paul, T.A., Chem. Rev., 2007, vol. 107, p. 2167. https://doi.org/10.1021/cr0783784
Horvath, T.I., Chem. Rev., 2002, vol. 35, p. 685. https://doi.org/10.1021/ar020160a
Lindström, U.K., Chem. Rev., 2002, vol. 102, p. 2751. https://doi.org/10.1021/cr010122p
Li, C.J., Chem. Rev., 2005, vol. 105, p. 3095. https://doi.org/10.1021/cr030009u
Li, C.J., Chem. Rev., 1993, vol. 93, p. 2023. https://doi.org/10.1021/cr00022a004
Li, C.J. and Chen, L., Chem. Soc. Rev., 2006, vol. 35, p. 68. https://doi.org/10.1039/B507207G
Dallinger, D. and Kappe, C.O., Chem. Rev., 2007, vol. 107, p. 2563. https://doi.org/10.1021/cr0509410
Chanda, A. and Fokin, V.V., Chem. Rev., 2009, vol. 109, p. 725. https://pubs.acs.org/doi/abs/10.1021/cr800448q
Klijn, J.E., Engberts, J.B.F.N., Nature, 2005, vol. 435, p. 746. https://doi.org/10.1038/435746a
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
Rideout, D.C. and Breslow, R., J. Am. Chem. Soc., 1980, vol. 102, p. 7816. https://doi.org/10.1021/ja00546a048
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
Herrer, C.I., Yao, X., Li, Z., and Li, C.J., Chem. Rev., 2007, vol. 107, p. 2546. https://doi.org/10.1021/cr050980b
Zhou, F. and Li, C.J., Nat. Commun., 2014, vol. 5, p. 4254. https://doi.org/10.1038/ncomms5254
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
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
Ghose, A.K., Viswanadhan, V.N., and Wendoloski, J.J., J. Comb. Chem., 1999, vol. 1, p. 55. https://doi.org/10.1021/cc9800071
Hein, D.W., Alheim, R.J., and Leavitt, J.J., J. Am. Chem. Soc., 1957, vol. 79, p. 427. https://doi.org/10.1021/ja01559a053
Chi, Y.C. and Sun, C.M., Synlett, 2000, p. 591. https://doi.org/10.1055/s-0029-1219374
Dudd, L., Venardou, M.E., Garcia-Verdugo, E., Licence, P., Blake, A.J., Wilson, C., and Poliakoff, M., Green Chem., 2003, vol. 5, p. 187. https://doi.org/10.1039/B212394K
Ben Alloum, A., Bougrin, K., and Soufiaoui, M., Tetrahedron Lett., 2003, vol. 44, p. 5935. https://doi.org/10.1016/S0040-4039(03)01387-X
Gogoi, P. and Konwar, D., Tetrahedron Lett., 2006, vol. 47, p. 79. https://doi.org/10.1016/j.tetlet.2005.10.134
Penetration, B., J. Med. Chem., 2009, vol. 52, p. 2341. https://doi.org/10.1021/jm801315b
Horton, D.A., Bourne, G.T., and Smythe, M.L., Chem. Rev., 2003, vol. 103, p. 893. https://doi.org/10.1021/cr020033s
Boiani, M. and González, M., Mini-Rev. Med. Chem., 2005, vol. 5, p. 409. https://doi.org/10.1021/jm801315b10.2174/1389557053544047
Preston, P.N., Chem. Rev., 1974, vol. 74, p. 279. https://doi.org/10.1021/cr60289a001
Denny, W.A., Rewcastle, G.W., and Baguley, B.C., J. Med. Chem., 1990, vol. 33, p. 814. https://doi.org/10.1021/jm801315b10.1021/jm00164a054
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
Reddy, Y.D., Reddy, Ch.V.R., and Dubey, P.K., RSC Adv., 2014, vol. 4, p. 2974. https://doi.org/10.1039/C3RA44423F
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
The authors declare no conflict of interest.
Rights and permissions
About this article
Cite this article
Narayana, B.S., Reddy, Y.D. & Reddy, C.V.R. Eco-friendly, Water Mediated, One-Pot Synthesis of 2-(5,6-Dicyano-1H-benzo[d]imidazol-2-yl)-N-arylbenzamides and Their Antifungal Activity Testing. Russ J Org Chem 59, 305–311 (2023). https://doi.org/10.1134/S1070428023020124
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070428023020124