Abstract
A diversity-oriented, green, and eco-friendly synthesis of 5,5′-(indolylmethylene)bis(2,2-dimethyl-1,3-dioxane-4,6-dione) derivatives has been developed by traditional condensation of 3-(1,4-dioxo-1,2,3,4-tetrahydrophthalazin-2-yl)-3-oxopropanenitrile, 1,5-substituted indole-3-carbaldehydes, and Meldrum’s acid under green conditions. An exciting feature of this condensation is that the product structure is determined by the catalyst used. The reaction features easy workup, excellent yields, and the use of water as green solvent.
Similar content being viewed by others
REFERENCES
Sunderhaus, J.D. and Martin, S.F., Chem. Eur. J., 2009, vol. 15, p. 1300. https://doi.org/10.1002/chem.200802140
Wang, Q., Wang, D.-X., Wang, M.-X., and Zhu, J., Acc. Chem. Res., 2018, vol. 51, p. 1290. https://doi.org/10.1021/acs.accounts.8b00105
Heravi, M.M., Asadi, S., and Lashkariani, B.M., Mol. Diversity, 2013, vol. 17, p. 389. https://doi.org/10.1007/s11030-013-9439-9
Alvim, G.O.H., da Silva, E.N., Jr., and Neto, B.A.D., RSC Adv., 2014, vol. 4, p. 54282. https://doi.org/10.1039/C4RA10651B
Wan, J.P. and Liu, Y., RSC Adv., 2012, vol. 2, p. 9763. https://doi.org/10.1039/C2RA21406G
Zhang, D.H., Zhang, Z., and Shi, M., Chem. Commun., 2012, vol. 48, p. 10271. https://doi.org/10.1039/C2CC34739C
Jeschke, P., Pest Manage. Sci., 2018, vol. 74, p. 282. https://doi.org/10.1002/ps.4755
Graves, D.B., J. Phys. D: Appl. Phys., 2012, vol. 45, article no. 263001. https://doi.org/10.1088/0022-3727/45/26/263001
Nagaraju, K., Lalitha, G., Suresh, M., Kranthi Kumar, G., and Sreekantha, B.J., Molecules, 2020, vol. 25, article no. 1909. https://doi.org/10.3390/molecules25081909
Combs, D.W., Rampulla, M.S., Demers, J.P., Falotico, R., and Moore, J.B., J. Med. Chem., 1992, vol. 35, p. 172. https://doi.org/10.1021/jm00079a022
Siddiqui, N., Alam, M., and Ahsan, W., Acta Pharm., 2008, vol. 58, p. 445. https://doi.org/10.2478/v10007-008-0025-0
Tweedie, D.J., Erikson, J.M., and Prough, R.A., Pharmacol. Ther., 1987, vol. 34, p. 111. https://doi.org/10.1016/0163-7258(87)90095-7
Munín, J., Quezada, E., Campos-Toimil, M., Cano, E., Uriarte, E., and Vina, D., Med. Chem. Res., 2017, vol. 26, p. 1682. https://doi.org/10.1007/s00044-017-1879-9
Wasfy, A.F., Aly, A.A., Behalo, M.S., and Mohamed, N.S., J. Heterocycl. Chem., 2020, vol. 15, p. 12. https://doi.org/10.1002/jhet.3735
Ghahremani, M., Davarpanah, J., Rezaee, P., and Davoodi, G., Res. Chem. Intermed., 2020, vol. 46, p. 2683. https://doi.org/10.1007/s11164-020-04114-x
Suman, M., Vijayabhaskar, B., Syam Kumar, U.K., and Venkateswara Rao, B., Russ. J. Gen. Chem., 2017, vol. 87, p. 2039. https://doi.org/10.1134/S1070363217090201
Veeranarayana Reddy, M., Radha Rani, C., and Yeon, T.J., Tetrahedron, 2014, vol. 70, p. 3762. https://doi.org/10.1016/j.tet.2014.04.044
Biabangard, A. and Shaterian, H.R., J. Iran. Chem. Soc., 2015, vol. 12, p. 1529. https://doi.org/10.1007/s13738-015-0623-y
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 colleagues at Dr. Reddy’s Laboratories Private Limited.
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
Reddy, V.H.K., Rao, A.V. Unexpected Formation of Indolylmethylene Bis-Meldrum’s Acid Derivatives under Green Conditions. Russ J Org Chem 58, 1348–1353 (2022). https://doi.org/10.1134/S1070428022090226
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070428022090226