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An Efficient One-Pot Three-Component Synthesis of Naphthyl-Substituted 5H-Chromeno[2,3-b]pyridine Derivatives under Solvent-Free Conditions

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Abstract

An efficient one-pot three-component reaction for the synthesis of 5-[naphthalen-1(2)yl]-5H-chromeno[2,3-b]pyridine derivatives has been developed. The synthesis was achieved by reacting salicyl­aldehydes, 2-aminopropene-1,1,3-tricarbonitrile, and naphthols catalyzed by triethylamine under solvent-free conditions at 120°C. The reaction involves formation of two C–C bonds, one C–O bond, and one C–N bond in a single synthetic operation. The final products can be isolated by simple filtration after treatment of the reaction mixture with ethanol. This rapid one-pot reaction does not require chromatographic purification and provides the products in good yields.

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REFERENCES

  1. Srivastava, S.K., Tripathi, R.P., and Ramachandran, R., J. Biol. Chem., 2005, vol. 280, p. 30273. https://doi.org/10.1074/jbc.M503780200

    Article  CAS  PubMed  Google Scholar 

  2. Brotz-Oesterhelt, H., Knezevic, I., Bartel, S., Lampe, T., Warnecke-Eberz, U., Ziegelbauer, K., Häbich, D., and Labischinski, H., J. Biol. Chem., 2003, vol. 278, p. 39435. https://doi.org/10.1074/jbc.M306479200

    Article  CAS  PubMed  Google Scholar 

  3. Kolokythas, G., Pouli, N., Marakos, P., Pratsinis, H., and Kletsas, D., Eur. J. Med. Chem., 2006, vol. 41, p. 71. https://doi.org/10.1016/j.ejmech.2005.10.011

    Article  CAS  PubMed  Google Scholar 

  4. Azuine, M.A., Tokuda, H., Takayasu, J., Enjyo, F., Mukainaka, T., Konoshima, T., Nishino, H., and Kapadia, G.J., Pharmacol. Res., 2004, vol. 49, p. 161. https://doi.org/10.1016/j.phrs.2003.07.014

    Article  CAS  PubMed  Google Scholar 

  5. Ukawa, K., Ishiguro, T., Kuriki, H., and Nohara, A., Chem. Pharm. Bull., 1985, 33, p. 4432. https://doi.org/10.1248/cpb.33.4432

  6. Makino, H., Saijo, T., Ashida, Y., Kuriki, H., and Maki, Y., Int. Arch. Allergy Appl. Immunol., 1987, vol. 82, p. 66. https://doi.org/10.1159/000234292

    Article  CAS  PubMed  Google Scholar 

  7. Maeda, A., Tsuruoka, S., Kanai, Y., Endou, H., Saito, K., Miyamoto, A., and Fujimura, A., Eur. J. Pharmacol., 2008, vol. 596, p. 166. https://doi.org/10.1016/j.ejphar.2008.08.023

    Article  CAS  PubMed  Google Scholar 

  8. Oset-Gasque, M.G., Gonzáles, M.P., Péres-Peña, J.P., Garcia-Font, N., Romero, A., del Pino, J., Ramos, E., Hadjipavlou-Litina, D., Soriano, E., Chioua, M., Samadi, A., Raghuvanshi, D.S., Singh, K.M., and Marco-Contelles, J., Eur. J. Med. Chem., 2014, vol. 74, p. 491. https://doi.org/10.1016/j.ejmech.2013.12.021

    Article  CAS  PubMed  Google Scholar 

  9. Anderson, D.R., Hegde, S., Reinhard, E., Gomez, L., Vernier, W.F., Lee, L., Liu, S., Sambandam, A., Snider, P. A., and Masih, L., Bioorg. Med. Chem. Lett., 2005, vol. 15, p. 1587. https://doi.org/10.1016/j.bmcl.2005.01.067

    Article  CAS  PubMed  Google Scholar 

  10. Chuang, F.K., Huang, S.M., Liao, C.L., Lee, A.R., Lien, S.P., Chiu, Y.L., Chang, T.H., Tsai, P.L., Lin, R.J., Shih, C.C., Tsai, Y.J., Lin, G.J., and Yen, L.C., Antimicrob. Agents Chemother., 2020, vol. 64, article ID e00941-19. https://doi.org/10.1128/AAC.00941-19

  11. Elinson, M.N., Vereshchagin, A.N., Anisina, Y.E., and Egorov, M.P., Polycyclic Aromat. Compd., 2020, vol. 40, p. 108. https://doi.org/10.1080/10406638.2017.1363062

    Article  CAS  Google Scholar 

  12. Elinson, M.N., Vereshchagin, A.N., Anisina, Y.E., Krymov, S.K., Fakhrutdinov, A.N., and Egorov, M.P., Monatsh. Chem., 2019, vol. 150, p. 1073. https://doi.org/10.1007/s00706-019-02388-5

    Article  CAS  Google Scholar 

  13. Elinson, M., Vereshchagin, A., Anisina, Y., Krymov, S., Fakhrutdinov, A., and Egorov, M., Arkivoc, 2019, vol. 2019, part (ii), p. 38. https://doi.org/10.24820/ark.5550190.p011.002

    Article  CAS  Google Scholar 

  14. Vereshchagin, A.N., Elinson, M.N. Anisina, Y.E., Ryzhkov, F.V., Goloveshkin, A.S., Novikov, R.A., and Egorov, M.P., J. Mol. Struct., 2017, vol, 1146, p. 766. https://doi.org/10.1016/j.molstruc.2017.06.044

  15. Elinson, M.N., Ryzhkov, F.V., Korolev, V.A., and Egorov, M.P., Heterocycl. Commun., 2016, vol. 22, p. 11. https://doi.org/10.1515/hc-2015-0232

    Article  CAS  Google Scholar 

  16. Elinson, M.N., Nasybullin, R.F., Ryzhkov, F.V., Zaimovskaya, T.A., and Nikishin, G.I., Monatsh. Chem., 2015, vol. 146, p. 631. https://doi.org/10.1007/s00706-014-1318-2

    Article  CAS  Google Scholar 

  17. Mishra, S. and Ghosh, R., Synth. Commun., 2012, vol. 42, p. 2229. https://doi.org/10.1080/00397911.2011.555284

    Article  CAS  Google Scholar 

  18. Evdokimov, N.M., Kireev, A.S., Yakovenko, A.A., Antipin, M.Y., Magedov, I.V., and Kornienko, A., Tetrahedron Lett., 2006, vol. 47, p. 9309. https://doi.org/10.1016/j.tetlet.2006.10.110

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  19. Elinson, M.N., Gorbunov, S.V., Vereshchagin, A.N., Nasybullin, R.F., Goloveshkin, A.S., Bushmarinov, I.S., and Egorov, M.P., Tetrahedron, 2014, vol. 70, p. 8559. https://doi.org/10.1016/j.tet.2014.09.066

    Article  CAS  Google Scholar 

  20. O’Callaghan, C.N., McMurry, T.B., and O’Brien, J.E., J. Chem. Soc., Perkin Trans. 1, 1995, p. 417. https://doi.org/10.1039/P19950000417

  21. Vereshchagin, A.N., Elinson, M.N., Anisina, Y.E., Ryzhkov, F.V., Novikov, R.A., and Egorov, M.P., ChemistrySelect, 2017, vol. 2, p. 4593. https://doi.org/10.1002/slct.201700606

    Article  CAS  Google Scholar 

  22. Chung, S.T., Huang, W.H., Huang, C.K., Liu, F.C., Huang, R.Y., Wu, C.C., and Lee, A.R., Res. Chem. Intermed., 2016, vol. 42, p. 1195. https://doi.org/10.1007/s11164-015-2081-7

    Article  CAS  Google Scholar 

  23. Grice, K.A., Patil, R., Ghosh, A., Paner, J.D., Guer­rero, M.A., Camacho, E.J.M., Cao, P.S., Niyazi, A.H., Zainab, Z., Sommer, R.D., Waris, G., and Patil, S., New J. Chem., 2018, vol. 42, p. 1151. https://doi.org/10.1039/C7NJ03724D

    Article  CAS  Google Scholar 

  24. Elinson, M.N., Vereshchagin, A.N., Anisina, Y.E., Fakh­rutdinov, A.N., Goloveshkin, A.S., and Egorov, M.P., Eur. J. Org. Chem., 2019, vol. 2019, p. 4171. https://doi.org/10.1002/ejoc.201900240

    Article  CAS  Google Scholar 

  25. Elinson, M.N., Vereshchagin, A.N., Anisina, Y.E., Fakh­rutdinov, A.N., Goloveshkin, A.S., and Egorov, M.P., J. Fluorine Chem., 2018, vol. 213, p. 31. https://doi.org/10.1016/j.jfluchem.2018.06.008

    Article  CAS  Google Scholar 

  26. Olyaei, A., Shafie, Z., and Sadeghpour, M., Tetrahedron Lett., 2018, vol. 59, p. 3567. https://doi.org/10.1016/j.tetlet.2018.08.038

    Article  CAS  Google Scholar 

  27. Anderson, D.R., Hegde, S., Reinhard, E., Gomez, L., Vernier, W.F., Lee, L., Liu, S., Sambandam, A., Snider, P.A., and Masih, L. Bioorg. Med. Chem. Lett., 2015, vol. 15, p. 1587. https://doi.org/10.1016/j.bmcl.2005.01.067

    Article  CAS  Google Scholar 

  28. Olyaei, A., Vaziri, M., and Razeghi, R., Tetrahedron Lett., 2013, vol. 54, p. 1963. https://doi.org/10.1016/j.tetlet.2013.01.124

    Article  CAS  Google Scholar 

  29. Nagaraju, P., Reddy, P.N., Padmaja, P., and Ugale, V.G., Chem. Data Collect., 2020, vol. 30, article ID 100541. https://doi.org/10.1016/j.cdc.2020.100541

  30. Malathi, V., Shivani, S., Bhaskar, K., Ugale, V.G., Padmaja, P., and Reddy, P.N., Chem. Data Collect., 2021, vol. 33, article ID 100693. https://doi.org/10.1016/j.cdc.2021.100693

  31. Malathi, V., Reddy, P.N., and Padmaja, P., Lett. Org. Chem., 2021, vol. 18, p. 721. https://doi.org/10.2174/1570178617999201020215852

    Article  CAS  Google Scholar 

  32. Padmaja, P., Anireddy, J.S., and Reddy, P.N., Chem. Heterocycl. Compd., 2018, vol. 54, p. 812. https://doi.org/10.1007/s10593-018-2354-3

    Article  CAS  Google Scholar 

  33. Reddy, P.N. and Padmaja, P., Curr. Microwave Chem., 2018, vol. 5, p. 104. https://doi.org/10.2174/2213335605666180306114045

    Article  CAS  Google Scholar 

  34. Padmaja, P., Reddy, B.V.S., Jain, N., Mutheneni, S.R., Bollepelli, P., Polepalli, S., Rambabu, G., and Reddy, P.N., New J. Chem., 2016, vol. 40, p. 8305. https://doi.org/10.1039/C6N01580H

    Article  CAS  Google Scholar 

  35. Reddy, P.N., Padmaja, P., Reddy, B.R., Rambabu, G., and Kumar, P., Med. Chem. Res., 2016, vol. 25, p. 2093. https://doi.org/10.1007/s00044-016-1676-x

    Article  CAS  Google Scholar 

  36. Padmaja, P., Rao, G.K., Indrasena, A., Reddy, B.V.S., Pa­tel, N., Shaik, A.B., Reddy, N., Dubey, P.K., and Bhad­ra, M.P., Org. Biomol. Chem., 2015, vol. 13, p. 1404. https://doi.org/10.1039/C4OB02015D

  37. Reddy, P.N., Padmaja, P., Reddy, B.R., and Jadav, S.S., Med. Chem. Res., 2017, vol. 26, p. 2243. https://doi.org/10.1007/s00044-017-1927-5

    Article  CAS  Google Scholar 

  38. Malathi, V., Nagaraju, P., Padmaja, P., and Reddy, P.N., Chem. Data Collect., 2021, vol. 35, article ID 100749. https://doi.org/10.1016/j.cdc.2021.1000749

  39. Muralimohan, G., Padmaja, P., Aravind, S., and Reddy, P.N., Chem. Heterocycl. Compd., 2021, vol. 57, p. 1176. https://doi.org/10.1007/s10593-021-03040-z

    Article  CAS  Google Scholar 

  40. Shaabani, A. and Hooshmand, S.E., Mol. Diversity, 2018, vol. 22, p. 207. https://doi.org/10.1007/s11030-017-9807-y

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Department of Chemistry, School of Science, Gitam University, 502329, Hyderabad, Telangana, India

    K. Nissi Sharon, M. Tarun, E. Sumanth & P. Narayana Reddy

  2. Centre for SemioChemicals, CSIR—Indian Institute of Chemical Technology, 500076, Hyderabad, Telangana, India

    P. Padmaja

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  1. K. Nissi Sharon
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Sharon, K.N., Padmaja, P., Tarun, M. et al. An Efficient One-Pot Three-Component Synthesis of Naphthyl-Substituted 5H-Chromeno[2,3-b]pyridine Derivatives under Solvent-Free Conditions. Russ J Org Chem 59, 470–477 (2023). https://doi.org/10.1134/S1070428023030156

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