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Green Approach for the Synthesis of 3-(3-Arylprop-2-enoyl)-2-hydroxycyclohepta-2,4,6-trien-1-ones

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Abstract

A facile and eco-friendly method for the synthesis of 3-(3-arylprop-2-enoyl)-2-hydroxycyclohepta-2,4,6-trien-1-ones via Claisen–Schmidt condensation of 3-acetyl-2-hydroxycyclohepta-2,4,6-trien-1-one and substituted benzaldehydes in the presence of anhydrous barium hydroxide (C-200) under grinding conditions has been described. This protocol is much more efficient as the reactions are carried out with high yields at room temperature, and the usage of hazardous chemicals is avoided at any stage of the reaction.

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REFERENCES

  1. Liu, N., Song, C., Schienebeck, M., Zhang, M., and Tang, W., Tetrahedron, 2014, vol. 70, p. 9281. https://doi.org/10.1016/j.tet.2014.07.065

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  2. Yamato, M., Ando, J., Sakai, J., Hashigaki, K., Wataya, Y., Tsukagoshi, S., Tashiro, T. and Tsuruo, T., J. Med. Chem., 1992, vol. 35, p. 267. https://doi.org/10.1021/jm00080a010

    Article  CAS  PubMed  Google Scholar 

  3. Harris, G.H., Hoogsteen, K., Silverman, K.C., Raghoo­bar, S.L., Bills, G.F., Lingham, R.B., Smith, J.L., Dougherty, H.W., Cascales, C., and Paláez, F., Tetra­hedron, 1993, vol. 49, p. 2139. https://doi.org/10.1016/S0040-4020(01)80357-4

    Article  CAS  Google Scholar 

  4. Mayerl, F., Gao, Q., Huang, S., Klohr, S.E., Matson, J.A., Gustavson, D.R., Pirnik, D.M., Berry, R.L., Fairchild, C., and Rose, W.C., J. Antibiot., 1993, vol. 46, p. 1082. https://doi.org/10.7164/antibiotics.46.1082

    Article  CAS  Google Scholar 

  5. Miyamoto, D., Kusagaya, Y., Endo, N., Sometani, A., Takeo, S., Suzuki, T., Arima, Y., Nakajima, K., and Suzuki, Y., Antiviral Res., 1998, vol. 39, p. 89. https://doi.org/10.1016/S0166-3542(98)00034-5

    Article  PubMed  Google Scholar 

  6. Cai, P., Smith, D., Cunningham, B., Brown-Shimer, S., Katz, B., Pearce, C., Venables, D., and Houck, D., J. Nat. Prod., 1998, vol. 61, p. 791. https://doi.org/10.1021/np9800506

    Article  CAS  PubMed  Google Scholar 

  7. Lange, U., Schumann, C., and Schmidt, K.L., Eur. J. Med. Res., 2001, vol. 6, p. 150.

    CAS  PubMed  Google Scholar 

  8. Matsumura, E., Morita, Y., Date, T., Tsujibo, H., Yasuda, M., Okabe, T., Ishida, N., and Inamori, Y., Biol. Pharm. Bull., 2001, vol. 24, p. 299. https://doi.org/10.1248/bpb.24.299

    Article  CAS  PubMed  Google Scholar 

  9. Baldwin, J.E., Mayweg, A.V.W., Pritchard, G.J., and Ad­lington, R.M., Tetrahedron Lett., 2003, vol. 44, p. 4543. https://doi.org/10.1016/S0040-4039(03)00987-0

    Article  CAS  Google Scholar 

  10. Mesa-Siverio, D., Estévez-Braun, A., Ravelo, Á.G., Murguia, J.R., and Rodríguez-Afonso, A., Eur. J. Org. Chem., 2003, vol. 2003, p. 4243. https://doi.org/10.1002/ejoc.200300284

    Article  CAS  Google Scholar 

  11. Dolle, R.E. and Nelson, K.H., J. Comb. Chem., 1999, vol. 1, p. 235. https://doi.org/10.1021/cc9900192

    Article  CAS  PubMed  Google Scholar 

  12. Angawi, F., Swenson, D.C., Gloer, J.B., and Wicklow, D.T., Tetrahedron Lett., 2003, vol. 44, p. 7593. https://doi.org/10.1016/j.tetlet.2003.08.057

    Article  CAS  Google Scholar 

  13. Ellington, E., Bastida, J., Viladomat, F., Simanek, V., and Codina, C., Biochem. Syst. Ecol., 2003, vol. 31, p. 715. https://doi.org/10.1016/S0305-1978(02)00248-X

    Article  CAS  Google Scholar 

  14. Liu, M., Wilairat, P., and Go, M.L., J. Med. Chem., 2001, vol. 44, p. 4443. https://doi.org/10.1021/jm0101747

    Article  CAS  PubMed  Google Scholar 

  15. Lee, S.H., Nan, J.X., Zhao, Y.Z., Woo, S.W., Park, E.J., Kang, T.H., Seo, G.S., Kim, Y.C., and Sohn, D.H., Planta Med., 2003, vol. 69, p. 990. https://doi.org/10.1055/s-2003-45143

    Article  CAS  PubMed  Google Scholar 

  16. Konieczny, M.T., Konieczny, W., Sabisz, M., Sklada­nowski, A., Wakiec, R., Augustynowicz-Kopec, E., and Zwolska, Z., Chem. Pharm. Bull., 2007, vol. 55, p. 817. https://doi.org/10.1248/cpb.55.817

    Article  CAS  Google Scholar 

  17. Jin, F., Jin, X.Y., Jin, Y.L., Sohn, D.W., Kim, S.A., Sohn, D.H., Kim, Y.C., and Kim, H.S., Arch. Pharm. Res., 2007, vol. 30, p. 1359. https://doi.org/10.1007/BF02977357

    Article  CAS  PubMed  Google Scholar 

  18. Narender, T., Khaliq, T., Shweta, Nishi, Goyal, N., and Gupta, S., Bioorg. Med. Chem., 2005, vol. 13, p. 6543. https://doi.org/10.1016/j.bmc.2005.07.005

    Article  CAS  PubMed  Google Scholar 

  19. Wu, J.H., Wang, X.H., Yi, Y.H., and Lee, K.H., Bioorg. Med. Chem. Lett., 2003, vol. 13, p. 1813. https://doi.org/10.1016/S0960-894X(03)00197-5

    Article  CAS  PubMed  Google Scholar 

  20. Nem, N.H., Kim, Y., Yu, Y.J., Hong, D.H., Kim, H.M., and Ahn, B.Z., Eur. J. Med. Chem., 2003, vol. 38, p. 179. https://doi.org/10.1016/S0223-5234(02)01443-5

    Article  CAS  Google Scholar 

  21. Harborne, J.B., Mabry, T.J., and Mabry, H., The Flavonoids, London: Chapmann & Hall, 1975.

  22. Chang, M., Li, Y., Zhang, H., and Gao, W., J. Chem. Res., 2010, p. 269. https://doi.org/10.3184/030823410X12740293863464

  23. Imafuku, K. and Yamaguchi, K., Bull. Chem. Soc. Jpn., 1981, vol. 54, p. 2855. https://doi.org/10.1246/bcsj.54.2855

    Article  CAS  Google Scholar 

  24. Honda, M. and Imafuku, K., Bull. Chem. Soc. Jpn., 1985, vol. 58, p. 508. https://doi.org/10.1246/bcsj.58.508

    Article  CAS  Google Scholar 

  25. Gao, W.T. and Zheng, Z., Chin. Chem. Lett., 2000, vol. 6, p. 503.

    Google Scholar 

  26. Imafuku, K., Wang, D-L., and Jing, Z-T., J. Heterocycl. Chem., 1990, vol. 27, p. 891. https://doi.org/10.1002/jhet.5570270413

    Article  Google Scholar 

  27. Dhar, D.N. and Lal, J.B., J. Org. Chem., 1958, vol. 23, p. 1159. https://doi.org/10.1021/jo01102a021

    Article  CAS  Google Scholar 

  28. Reddy, G.V., Maitraie, D., Narsaiah, B., Rambabu, Y., and Rao, P.S., Synth. Commun., 2001, vol. 31, p. 2881. https://doi.org/10.1081/SCC-100105339

    Article  CAS  Google Scholar 

  29. Pore, D., Desai, U., Thopte, T., and Wadgaonkar, P., Russ. J. Org. Chem., 2007, vol. 43, p. 1088. https://doi.org/10.1134/S107042800707024X

    Article  CAS  Google Scholar 

  30. Rajender, S.V., George, W.K., Lan, T.E., and Richard, M.P., Synth. Commun., 1985, vol. 15, p. 279. https://doi.org/10.1080/00397918508063800

    Article  Google Scholar 

  31. Domínguez, J.N., Charris, J.E., Lobo, G., de Domín­guez, N.G. de, Moreno, M.M., Riggione, F., Sanchez, E., Olson, J., and Rosenthal, P.J., Eur. J. Med. Chem., 2001, vol. 36, p. 555. https://doi.org/10.1016/S0223-5234(01)01245-4

    Article  PubMed  Google Scholar 

  32. Calloway, N.O. and Green, L.D., J. Am. Chem. Soc., 1937, vol. 59, p. 809. https://doi.org/10.1021/ja01284a011

    Article  CAS  Google Scholar 

  33. Breslow, D.S. and Hauser, C.R., J. Am. Chem. Soc., 1940, vol. 62, p. 2385. https://doi.org/10.1021/ja01866a035

    Article  CAS  Google Scholar 

  34. Kantam, M.L., Prakash, V.B., and Reddy, C.V., Synth. Commun., 2005, vol. 35, p. 1971. https://doi.org/10.1081/SCC-200065006

    Article  CAS  Google Scholar 

  35. Dave, S.S., Ghatole, A.M., Rahatgoankar, A.M., Chorghade, M.S., Chauhan, P.M.S., and Srivastava, K., Indian J. Chem., Sect. B, 2009, vol. 48, p. 1780. http://nopr.niscpr.res.in/handle/123456789/6865

    Google Scholar 

  36. Sirsat, S.B., Halikar, N.K., Pund, M.M., and Vartale, S.P., Res. J. Pharm., Biol. Chem. Sci., 2012, vol. 3, p. 240.

    CAS  Google Scholar 

  37. Tiwari, V., Ali, P., and Meshram, J., Green Chem. Lett. Rev., 2011, vol. 4, p. 219. https://doi.org/10.1080/17518253.2010.544262

    Article  CAS  Google Scholar 

  38. Tiwari, V., Ali, P., and Meshram, J., Int. J. ChemTech Res., 2010, vol. 2, p. 1031.

    CAS  Google Scholar 

  39. Zhu, H., Tang, L., Zhang, C., Wei, B., Yang, P., He, D., Zheng, L., and Zhang, Y., Front. Pharmacol., 2019, vol. 10, article no. 3141. https://doi.org/10.3389/fphar.2019.01341

  40. Bentahar, S., Taleb, M.A., Sabour, A., Dbik, A., Khomri, M.E., Messaoudi, N.E., and Lacherai, A., Russ. J. Appl. Chem., 2020, vol. 93, p. 983. https://doi.org/10.1134/S107042722007006X

    Article  CAS  Google Scholar 

  41. Adnan, D., Singh, B., Mehta, S.K., Kumar, V., and Kataria, R., Curr. Res. Green Sustainable Chem., 2020, vol. 3, article ID 100041. https://doi.org/10.1016/j.crgsc.2020.100041

  42. Chaker, H., Ferouani, G., Chikhi, I., Djennas, M., and Fourmentin, S., Colloid Interface Sci. Commun., 2021, vol. 43, article ID 100461. https://doi.org/10.1016/j.colcom.2021.100461

  43. Selvaraj, G.G., Jayaraman, S., Selvarasu, U., Velu­mani, B.P., and Parasuraman, K., Curr. Catal., 2021, vol. 10, p. 103. https://doi.org/10.2174/2211544710666210716113451

    Article  CAS  Google Scholar 

  44. Ekanayake, U.G.M., Weerathunga, H., Weerasinghe, J., Waclawik, E.R., Sun, Z., MacLeod, J.M., O’Mul­lane, A.P., and Ostrikov, K.K., Sustainable Mater. Technol., 2022, vol. 32, article ID e00394. https://doi.org/10.1016/j.susmat.2022.e00394

  45. Sharma, D., Kumar, S., and Makrandi, J.K., Green Chem. Lett. Rev., 2015, vol. 8, p. 21. https://doi.org/10.1080/17518253.2015.1058975

    Article  CAS  Google Scholar 

  46. Sharma, D. and Kumar, S., Bulg. Chem. Commun., 2017, vol. 49, p. 309.

    Google Scholar 

  47. Sharma, D., Res. Chem. Intermed., 2015, vol. 41, p. 927. https://doi.org/10.1007/s11164-013-1245-6

    Article  CAS  Google Scholar 

  48. Alcantara, D.R., Marinas, J.M., and Sinisterra, J.V., Tetrahedron Lett., 1987, vol. 28, p. 1515. https://doi.org/10.1016/S0040-4039(01)81030-3

    Article  CAS  Google Scholar 

  49. Imafuku, K., Yamane, A., and Matsumura, H., J. Synth. Org. Chem., 1980, vol. 38, p. 308. https://doi.org/10.5059/yukigoseikyokaishi.38.308

    Article  Google Scholar 

  50. Gao, W., Zheng, Z., and Chen, H., Acta Sci. Nat. Univ. Pekin., 2001, vol. 37, p. 205.

    CAS  Google Scholar 

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ACKNOWLEDGMENTS

The author is very much grateful to Prof. Dr. J.K. Makrandi (retired), Department of Chemistry, Maharishi Dayanand University, Rohtak, India, for his endless support to carry out this research work.

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  1. Department of Chemistry, Kishan Lal Public College, 123401, Rewari, India

    D. Kumar

  2. Department of Chemistry, Vaish (P.G.) College, 127021, Bhiwani, India

    K. K. Sharma

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Kumar, D., Sharma, K.K. Green Approach for the Synthesis of 3-(3-Arylprop-2-enoyl)-2-hydroxycyclohepta-2,4,6-trien-1-ones. Russ J Org Chem 59, 1231–1236 (2023). https://doi.org/10.1134/S1070428023070151

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