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One-Pot Green Synthesis of 2-Hydroxybenzoyl(cinnamoyl)methanes and 2-Styrylchromones Using Dual-Frequency Ultrasonication

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Abstract

One-pot green synthesis of (2-hydroxybenzoyl)(cinnamoyl)methanes has been performed by reacting 2-hydroxyacetophenones with cinnamoyl chlorides using activated Ba(OH)2, followed by Baker–Venkataraman rearrangement assisted by dual-frequency ultrasonication. Cyclization of (2-hydroxybenzoyl)(cinnamoyl)methanes using methanesulfonic acid along with dual-frequency ultrasound irradiation resulted in the formation of 2-strylchromones in a single step. The products were obtained with high yields, and their structures were confirmed by NMR and IR spectral data.

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REFERENCES

  1. Ghosal, S., Singh, S., Bhagat, M.P., and Kumar, Y., Phytochemistry, 1980, vol. 21, p. 2943. https://doi.org/10.1016/0031-9422(80)85074-6

    Article  Google Scholar 

  2. Chemistry of Heterocyclic Compounds: Chromenes, Chromanones, and Chromones, Ellis, G.P., Ed., 1977, vol. 31, p. 455. https://doi.org/10.1002/9780470187012

  3. Xing, Q., Liang, H., Bao, M., Li, X., Zhang, J., Bi, T., Zhang, Y., Xu, J., Du, Y., and Zhao, K., Adv. Synth. Catal., 2019, vol. 361, p. 4669. https://doi.org/10.1002/adsc.201900652

    Article  CAS  Google Scholar 

  4. Bala, M., Kumar, S., Taxak, V.B., Boora, P., and Khatkar, S.P., J. Mater. Sci.: Mater. Electron., 2016, vol. 27, p. 9306. https://doi.org/10.1007/s10854-016-4970-y

    Article  CAS  Google Scholar 

  5. Crouse, G.D., McGowan, M.J., and Boisvenue, R.J., J. Med. Chem., 1989, vol. 32, p. 2148. https://doi.org/10.1021/jm00129a021

    Article  CAS  PubMed  Google Scholar 

  6. Andrae, I., Bringhen, A., Böhm, F., Gonzenbach, H., Hill, T., Mulroy, L., and Truscott, T.G., J. Photochem. Photobiol., B, 1997, vol. 37, p. 147. https://doi.org/10.1016/S1011-1344(96)07330-7

    Article  CAS  Google Scholar 

  7. Pinto, J., Silva, V.L., Silva, A.M., and Silva, A., Molecules, 2015, vol. 20, p. 11418. https://doi.org/10.3390/molecules200611418

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  8. Doria, G., Romeo, C., Forgione, A., Sberze, P., Tibolla, N., Corno, M.L., Cruzzola, G., and Cadelli, G., Eur. J. Med. Chem., 1979, vol. 14, p. 347.

    CAS  Google Scholar 

  9. Gerwick, W.H., J. Nat. Prod., 1989, vol. 52, no. 2, p. 252. https://doi.org/10.1021/np50062a005

    Article  CAS  PubMed  Google Scholar 

  10. Gerwick, W.H., Lopez, A., Van Dyune, G.D., Clardy, J., Ortiz, W., and Baez, A., Tetrahedron Lett., 1986, vol. 27, p. 1979. https://doi.org/10.1016/s0040-4039(00)84426-3

    Article  CAS  Google Scholar 

  11. Shaw, A.Y., Chang, C.Y., Liau, H.H., Lu, P.J., Chen, H.L., Yang, C.N., and Li, H.Y., Eur. J. Med. Chem., 2009, vol. 44, p. 2552. https://doi.org/10.1016/j.ejmech.2009.01.034

    Article  CAS  PubMed  Google Scholar 

  12. Gomes, A., Fernandes, E., Silva, A.M.S., Santos, C.M.M., Pinto, D.C.G.A., Cavaleiro, J.A.S., and Lima, J.L., Bioorg. Med. Chem., 2007, vol. 15, no. 18, p. 6027. https://doi.org/10.1016/j.bmc.2007.06.046

    Article  CAS  PubMed  Google Scholar 

  13. Gomes, A., Fernandes, E., Silva, A.M.S., Pinto, D.C.G.A., Santos, C.M.M., Cavaleiro, J.A.S., and Lima, J.L.F.C., Biochem. Pharmacol., 2009, vol. 78, no. 2, p. 171. https://doi.org/10.1016/j.bcp.2009.03.028

    Article  CAS  PubMed  Google Scholar 

  14. Desideri, N., Mastromarino, P., and Conti, C., Antiviral Chem. Chemother., 2003, vol. 14, no. 4, p. 195. https://doi.org/10.1177/095632020301400404

    Article  CAS  Google Scholar 

  15. Santos, C.M., Proença, C., Freitas, M., Araújo, A.N., Silva, A., and Fernandes, E., Abstracts of Papers, Bioheterocycles 2019—XVIII Int. Conf. on Heterocycles in Bioorganic Chemistry, 2019, p. 68.

  16. Takao, K., Endo, S., Nagai, J., Kamauchi, H., Takemura, Y., Uesawa, Y., and Sugita, Y., Bioorg. Chem., 2019, vol. 92, article ID 103285. https://doi.org/10.1016/j.bioorg.2019.103285

  17. Dunne, A.T.M., Gowan, J.E., Keane, J., O’Kelly, B.M., O’Sullivan, D., Roche, M.M., Ryan, P.M., and Wheeler, T.S., J. Chem. Soc., 1950, p. 1252. https://doi.org/10.1039/JR9500001252

  18. Mahal, H.S. and Venkataraman, K., J. Chem. Soc., 1934, vol. 387, p. 1767. https://doi.org/10.1039/JR9340001767

    Article  Google Scholar 

  19. Kumar, A. and Makrandi, J.K., Heterocycl. Lett., 2012, vol. 2, p. 271.

    CAS  Google Scholar 

  20. Pinto, D.C., Silva, A.M., and Cavaleiro, J.A., New J. Chem., 2000, vol. 24, p. 85. https://doi.org/10.1039/A908539D

    Article  CAS  Google Scholar 

  21. Sharma, D., Kumar, S., and Makrandi, J.K., Green Chem. Lett. Rev., 2009, vol. 2, p. 53. https://doi.org/10.1080/17518250903002343

    Article  CAS  Google Scholar 

  22. Königs, P., Neumann, O., Kataeva, O., Schnakenburg, G., and Waldvogel, S.R., Eur. J. Org. Chem., 2010, vol. 33, p. 6417. https://doi.org/10.1002/ejoc.201000957

    Article  CAS  Google Scholar 

  23. Pinto, D.C., Silva, A.M., and Cavaleiro, J.A., Synlett, 2007, vol. 12, p. 1897. https://doi.org/10.1055/s-2007-984525

    Article  CAS  Google Scholar 

  24. St-Gelais, A., Alsarraf, J., Legault, J., Gauthier, C., and Pichette, A., Org. Lett., 2018, vol. 20, p. 7424. https://doi.org/10.1021/acs.orglett.8b03148

    Article  CAS  PubMed  Google Scholar 

  25. Goel, S., Ritu, and Makrandi, J.K., Indian J. Chem., Sect. B, 2006, vol. 45, p. 1278. http://nopr.niscair.res.in/handle/123456789/30698

    Google Scholar 

  26. Makrandi, J.K. and Kumari, V., Synth. Commun., 1989, vol. 19, p. 1919. https://doi.org/10.1080/00397918908052583

    Article  CAS  Google Scholar 

  27. Pinto, D.C., Silva, A.M., Almeida, L.M., Cavaleiro, J.A., Lévai, A., and Patonay, T., J. Heterocycl. Chem., 1998, vol. 35, no. 1, p. 217. https://doi.org/10.1002/jhet.5570350140

    Article  CAS  Google Scholar 

  28. Sharma, D. and Makrandi, J.K., Green Chem. Lett. Rev., 2009, vol. 2, no. 3, p. 157. https://doi.org/10.1080/17518250903241966

    Article  CAS  Google Scholar 

  29. Makrandi, J.K. and Seema, Chem. Ind., 1989, p. 607.

  30. Makrandi, J.K. and Seema, Indian J. Chem., Sect. B, 1991, vol. 30, p. 788.

    Google Scholar 

  31. Mirkhani, V., Moghadam, M., Tangestaninejad, S., Mohammadpoor-Baltork, I., and Mahdavi, M., Monatsh. Chem., 2009, vol. 140, p. 1489. https://doi.org/10.1007/s00706-009-0213-8

    Article  CAS  Google Scholar 

  32. Sadjadi, S. and Sepehrian, H., Ultrason. Sonochem., 2011, vol. 18, p. 480. https://doi.org/10.1016/j.ultsonch.2010.08.004

    Article  CAS  PubMed  Google Scholar 

  33. Feng, H., Ying, X., Peng, Y., Van der Eycken, E.V., Liu, C., Zhao, S., and Song, G., Monatsh. Chem., 2013, vol. 144, p. 681. https://doi.org/10.1007/s00706-012-0846-x

    Article  CAS  Google Scholar 

  34. Zeng, H., Li, H., and Shao, H., Ultrason. Sonochem., 2009, vol. 16, p. 758. https://doi.org/10.1016/j.ultsonch.2009.03.008

    Article  CAS  PubMed  Google Scholar 

  35. Kumar, S., Chem. Sci. Trans., 2015, vol. 4, p. 258. https://doi.org/10.7598/cst2015.978

    Article  CAS  Google Scholar 

  36. Kumar, S. and Sharma, D.K., Green Process. Synth., 2017, vol. 6, no. 1, p. 73. https://doi.org/10.1515/gps-2016-0099

    Article  CAS  Google Scholar 

  37. Sasidharan, S., Raj, S., Sonawane, S., Pinjari, D., Pandit, A.B., and Saudagar, P., Nanomater. Synth., 2019, p. 27. https://doi.org/10.1016/B978-0-12-815751-0.00002-X

  38. Salvador, R.A.J., Sa e Melo, L.M., Neves, S.A., and Campos, A.S., Tetrahedron Lett., 1993, vol. 34, p. 357. https://doi.org/10.1016/S0040-4039(00)60587-7

    Article  CAS  Google Scholar 

  39. Zhang, Z., Zha, Z., Gan, C., Pan, C., Zhou, Y., Wang, Z., and Zhou, M.M., J. Org. Chem., 2006, vol.71, p. 4339. https://doi.org/10.1021/jo060372b

    Article  CAS  PubMed  Google Scholar 

  40. Tiwari, B.K., TrAC, Trends Anal. Chem., 2015, vol. 71, p. 100. https://doi.org/10.1016/j.trac.2015.04.013

  41. Baig, R.B.N. and Varma, R.S., Chem. Soc. Rev., 2012, vol. 41, p. 1559. https://doi.org/10.1039/C1CS15204A

    Article  CAS  PubMed  Google Scholar 

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Vashisth, N., Sharma, S.P., Kumar, S. et al. One-Pot Green Synthesis of 2-Hydroxybenzoyl(cinnamoyl)methanes and 2-Styrylchromones Using Dual-Frequency Ultrasonication. Russ J Org Chem 56, 2143–2147 (2020). https://doi.org/10.1134/S1070428020120155

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