Abstract
The synthesis of 2-(2-amino-4-(1H-indol-2-yl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonyl)-2,3-dihydrophthalazine-1,4-diones with good yields of 80–85% was accomplished by reacting diethyl phthalate, 2-cyanoacetohydrazide, 1H-indole-2-carbaldehydes, and 5,5-dimethylcyclohexane-1,3-dione in [BMIM]BF4 as ionic liquid medium at 70–75°C for 110–120 min. The product structure was characterized by NMR and mass spectrometry. The proposed synthetic strategy has the remarkable advantages of excellent yields, straightforward protocol, environmental friendliness, short reaction times, and mild reaction conditions. There is no need for catalyst or solvent since a catalytically active ionic liquid is used as a medium.
REFERENCES
Maddila, S.N., Maddila, S., Khumalo, M., Bhaskaruni, S.V.H.S., and Sreekantha, B.J., J. Mol. Struct., 2019, vol. 1185, p. 357. https://doi.org/10.1016/j.molstruc.2019.03.006
Chebanov, V.A., Muravyova, E.A., Desenko, S.M., Musatov, V.I., Knyazeva, I.V., Shishkina, S.V., Shishkin, O.V., and Kappe, C.O., J. Comb. Chem., 2006, vol. 8, p. 427. https://doi.org/10.1021/cc060021a
Nilsson, B.L. and Overman, L.E., J. Org. Chem., 2006, vol. 71, p. 7706. https://doi.org/10.1021/jo061199m
Chebanov, V.A., Saraev, V.E., Desenko, S.M., Chernenko, V.N., Shishkina, S.V., Shishkin, O.V., Kobzar, K.M., and Kappe, C.O., Org. Lett., 2007, vol. 9, p. 1691. https://doi.org/10.1021/ol070411l
De Silva, R.A., Santra, S., and Andreana, P.R., Org. Lett., 2008, vol. 10, p. 4541. https://doi.org/10.1021/ol801841m
Maddila, S., Sreekanta, B., Jonnalagadda, K.K.G., and Surya, N.M., Curr. Org. Synth., 2017, vol. 14, p. 643. https://doi.org/10.2174/1570179414666161208164731
Maddila, S., Gangu, K.K., Maddila, S.N., and Jonnalagadda, S.B., Mol. Diversity, 2017, vol. 21, p. 247. https://doi.org/10.1007/s11030-016-9708-5
Gangu, K.K., Maddila, S., and Jonnalagadda, S.B., New J. Chem., 2017, vol. 41, p. 6455. https://doi.org/10.1039/C7NJ00855D
Bhaskaruni, S.V.H.S., Maddila, S., Zyl, W.E., and Jonnalagadda, S.B., Catal. Commun., 2017, vol. 100, p. 24. https://doi.org/10.3390/molecules23071648
Shabalala, S., Maddila, S., Zyl, W.E., and Jonnalagadda, S.B., Catal. Commun., 2016, vol. 79, p. 21. https://doi.org/10.1039/C8RA01994K
Ma, C., Zhou, J.-Y., Zhang, Y.-Z., Jiao, Y., Mei, G.-J., and Shi, F., Chem. Asian J., 2018, vol. 13, p. 2549. https://doi.org/10.1002/asia.201800620
Gangu, K.K., Maddila, S., Maddila, S.N., and Jonnalagadda, S.B., RSC Adv., 2017, vol. 7, p. 423. https://doi.org/10.1039/c6ra25372e
Al’-Assar, F., Zelenin, K.N., Lesiovskaya, E.E., Bezhan, I.P., and Chakchir, B.A., Pharm. Chem. J., 2002, vol. 36, p. 598. https://doi.org/10.1023/A:1022665331722
Rambhau, P.G. and Ambarsing, P.R., Drug Invent. Today, 2013, vol. 5, p. 148. https://doi.org/10.1016/j.dit.2013.05.010
Dömling, A., Wang, W., and Wang, K., Chem. Rev., 2012, vol. 112, p. 3083. https://doi.org/10.1021/cr100233r
Tocco, G., Zedda, G., Casu, M., Simbula, G., and Begala, M., Molecules, 2017, vol. 22, article no. 1747. https://doi.org/10.3390/molecules22101747
Kidwai, M., Saxena, S., Khan, M.K.R., and Thukral, S.S., Bioorg. Med. Chem. Lett., 2005, vol. 15, p. 4295. https://doi.org/10.1016/j.bmcl.2005.06.041
Ustündağ, G.C., Şatana, D., and Zhan, G., J. Enzyme Inhib. Med. Chem., 2016, vol. 31, p. 369. https://doi.org/10.3109/14756366.2015.1024673
Pratap, R. and Ram, V.J., Chem. Rev., 2014, vol. 114, p. 10476. https://doi.org/10.1021/cr500075s
Ellis, G.P., The Chemistry of Heterocyclic Compounds, Weissberger, A. and Taylor, E.C., Eds., New York: Wiley, 1977, vol. 2, p. 11.
Hafez, E.A.A., Elnagdi, M.H., Elagamey, A.G.A., and El-Taweel, F.M.A.A., Heterocycles, 1987, vol. 26, p. 903. https://doi.org/10.3987/R-1987-04-0903
Oliveira-Pintoa, S., Ludovicoa, P., and Costa, M., Bioorg. Chem., 2020, vol. 100, article ID 103942. https://doi.org/10.1016/j.bioorg.2020.103942
Chen, Y.-J., Huang, Sh.-M., Tai, M.-Ch., Chen, J.-T., Lee, A.-R., Huang, R.-Y., and Liang, Ch.-M., Pharmacol. Rep., 2020, vol. 72, p. 115. https://doi.org/10.1007/s43440-019-00026-9
Hufford, C.D., Oguntimein, B.O., Van Engen, D., Muthard, D., and Clardy, J., J. Am. Chem. Soc., 1980, vol. 102, p. 7365. https://doi.org/10.1021/ja00544a037
Fuendjiep, V., Nkengfack, A.E., Fomum, Z.T., Sondengam, B.L., and Bodo, B., J. Nat. Prod., 1998, vol. 61, p. 380. https://doi.org/10.1021/np970187g
Wandji, J., Fomum, Z.T., Tillequin, F., Libot, F., and Koch, M., J. Nat. Prod., 1995, vol. 58, p. 105. https://doi.org/10.1021/np50115a013
Abdolmohammadi, S., Mirza, B., Vessally, E., RSC Adv., 2019, vol. 9, p. 41868. https://doi.org/10.1039/C9RA09031B
ACKNOWLEDGMENTS
The authors are thankful to the authorities of Maharaja Agrasen University, Baddi, for providing the necessary research facilities.
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
The authors declare no conflict of interest.
Supplementary information
Rights and permissions
About this article
Cite this article
Dhavaria, S., Dhiman, M. A Facile One-Pot Four-Component Green Synthesis of 4-(1H-Indol-2-yl)-4H-chromenes Conjugated with Phthalazine-1,4-diones. Russ J Org Chem 59, 726–732 (2023). https://doi.org/10.1134/S1070428023040231
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070428023040231