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Unexpected Formation of Indolylmethylene Bis-Meldrum’s Acid Derivatives under Green Conditions

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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.

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REFERENCES

  1. Sunderhaus, J.D. and Martin, S.F., Chem. Eur. J., 2009, vol. 15, p. 1300. https://doi.org/10.1002/chem.200802140

    Article  CAS  PubMed  Google Scholar 

  2. 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

    Article  CAS  PubMed  Google Scholar 

  3. 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

    Article  CAS  Google Scholar 

  4. 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

    Article  CAS  Google Scholar 

  5. Wan, J.P. and Liu, Y., RSC Adv., 2012, vol. 2, p. 9763. https://doi.org/10.1039/C2RA21406G

    Article  CAS  Google Scholar 

  6. Zhang, D.H., Zhang, Z., and Shi, M., Chem. Commun., 2012, vol. 48, p. 10271. https://doi.org/10.1039/C2CC34739C

    Article  CAS  Google Scholar 

  7. Jeschke, P., Pest Manage. Sci., 2018, vol. 74, p. 282. https://doi.org/10.1002/ps.4755

    Article  CAS  Google Scholar 

  8. Graves, D.B., J. Phys. D: Appl. Phys., 2012, vol. 45, article no. 263001. https://doi.org/10.1088/0022-3727/45/26/263001

  9. 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

  10. 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

    Article  CAS  PubMed  Google Scholar 

  11. Siddiqui, N., Alam, M., and Ahsan, W., Acta Pharm., 2008, vol. 58, p. 445. https://doi.org/10.2478/v10007-008-0025-0

    Article  CAS  PubMed  Google Scholar 

  12. 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

    Article  CAS  PubMed  Google Scholar 

  13. 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

    Article  CAS  Google Scholar 

  14. 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

    Article  CAS  Google Scholar 

  15. 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

    Article  CAS  Google Scholar 

  16. 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

    Article  CAS  Google Scholar 

  17. 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

    Article  CAS  Google Scholar 

  18. Biabangard, A. and Shaterian, H.R., J. Iran. Chem. Soc., 2015, vol. 12, p. 1529. https://doi.org/10.1007/s13738-015-0623-y

    Article  CAS  Google Scholar 

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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.

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Correspondence to V. Hari Krishna Reddy.

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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

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  • DOI: https://doi.org/10.1134/S1070428022090226

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