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A simple route for the synthesis of substituted thiazole derivatives by multicomponent reaction between arylglyoxals, acetylacetone or ethyl acetoacetate, and thiosemicarbazones

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Chemistry of Heterocyclic Compounds Aims and scope

An effective one-pot three-component protocol for the synthesis of polysubstituted thiazole derivatives is reported. The reaction proceeds between arylglyoxals, thiosemicarbazones, and acetylacetone or ethyl acetoacetate in ethanol as solvent and in the presence of acetic acid as catalyst.

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References

  1. Ganesh, T.; Schilling, J. K.; Palakodety, R. K.; Ravindra, R.; Shanker, N.; Bane, S.; Kingston, D. G. I. Tetrahedron 2003, 59, 9979.

    Article  CAS  Google Scholar 

  2. Nicolaou, K. C.; Ritzen, A.; Namoto, K. Chem. Commun. 2001, 1523.

  3. Hu, D.-J.; Liu, S.-F.; Huang, T.-H.; Tu, H.-Y.; Zhang, A.-D. Molecules 2009, 14, 1288.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  4. Van Muijlwijk-Koezen, J. E.; Timmerman, H.; Vollinga, R. C.; Frijtag von Drabbe Künzel, J.; de Groote, M.; Visser, S.; Ijzerman, A. P. J. Med. Chem. 2001, 44, 749.

  5. Mahboobi, S.; Sellmer, A.; Höcher, H.; Eichhorn, E.; Bar, T.; Schmidt, M.; Maier, T.; Stadlwieser, J. F.; Beckers, T. L. J. Med. Chem. 2006, 49, 5769.

    Article  CAS  PubMed  Google Scholar 

  6. Sultanova, R. M.; Lobov, A. N.; Shumadalova, A. V.; Meshcheryakova, S. A.; Zileeva, Z. R.; Khusnutdinova, N. S.; Vakhitov, V. A.; Vakhitova, Y. V. Nat. Prod. Res. 2021, 35, 1340.

    Article  CAS  PubMed  Google Scholar 

  7. Tsuji, K.; Ishikawa, H. Bioorg. Med. Chem. Lett. 1994, 4, 1601.

    Article  CAS  Google Scholar 

  8. Haviv, F.; Ratajczyk, J. D.; DeNet, R. W.; Kerdesky, F. A.; Walters, R. L.; Schmidt, S. P.; Holms, J. H.; Young, P. R.; Carter, G. W. J. Med. Chem. 1988, 31, 1719.

    Article  CAS  PubMed  Google Scholar 

  9. Miwatashi, S.; Arikawa, Y.; Kotani, E.; Miyamoto, M.; Naruo, K. I.; Kimura, H.; Yanaka, T.; Asahi, S.; Ohkawa, S. J. Med. Chem. 2005, 48, 5966.

    Article  CAS  PubMed  Google Scholar 

  10. Papadopoulou, C.; Geronikaki, A.; Hadjipavlou-Litina, D. Farmaco 2005, 60, 969.

    Article  CAS  PubMed  Google Scholar 

  11. Patt, W. C.; Hamilton, H. W.; Taylor, M. D.; Ryan, M. J.; Taylor, D. G. J.; Connolly, C. J. C.; Doherty, A. M.; Klutchko, S. R.; Sircar, I.; Steinbaugh, B. A.; Batley, B. L.; Painchaud, C. A.; Rapundalo, S. T.; Michniewicz, B. M.; Olson, S. C. J. J. Med. Chem. 1992, 35, 2562.

    Article  CAS  PubMed  Google Scholar 

  12. Tsuruni, Y.; Ueda, H.; Hayashi, K.; Takase, S.; Nishikawa, M.; Kiyoto, S.; Okuhara, M. J. Antibiotics 1995, 48, 1066.

    Article  Google Scholar 

  13. Bell, F. W.; Cantrell, A. S.; Hoegberg, M.; Jaskunas, S. R.; Johansson, N. G.; Jordan, C. L.; Kinnick, M. D.; Lind, P.; Morin, J. M., Jr.; Noveen, R.; Oberg, B.; Palkowitz, J. A.; Parrish, C. A.; Pranc, P.; Sahlberg, C.; Ternansky, R. J.; Vasileft, R. T.; Vrang, L.; West, S. J.; Zhang, H.; Zhou, X. Y. J. Med. Chem. 1995, 38, 4929.

    Article  CAS  PubMed  Google Scholar 

  14. Kumar, Y.; Green, R.; Borysko, K. Z.; Wise, D. S.; Wotring, L. L.; Townsend, L. B. J. Med. Chem. 1993, 36, 3843.

    Article  CAS  PubMed  Google Scholar 

  15. Ei-Subbagh, H. I.; Al-Obaid, A. M. Eur. J. Med. Chem. 1996, 31, 1017.

    Article  Google Scholar 

  16. Pereira, R.; Gaudon, C.; Iglesias, B.; Germain, P.; Gronemeyer, H.; de Lera, A. R. Bioorg. Med. Chem. Lett. 2006, 16, 49.

    Article  CAS  PubMed  Google Scholar 

  17. Potewar, T. M.; Ingale, S. A.; Srinivasan, K. V. Tetrahedron 2007, 63, 11066.

    Article  CAS  Google Scholar 

  18. Narender, M.; Reddy, M. S.; Sridhar, R.; Nageswar, Y. V. D.; Rao, K. R. Tetrahedron Lett. 2005, 46, 5953.

    Article  CAS  Google Scholar 

  19. Das, B.; Reddy, V. S.; Ramu, R. J. Mol. Catal. A: Chem. 2006, 252, 235.

    Article  CAS  Google Scholar 

  20. Liu, X. L.; Wang, Q. Y.; Sheng, S. R.; Xu, C.; Cai, M. Z. Synth. Commun. 2008, 38, 3338.

    Article  CAS  Google Scholar 

  21. Wei, S.; Weiß, K. M.; Tsogoeva, S. B. Synthesis 2012, 44, 3441.

    Article  CAS  Google Scholar 

  22. Weiß, K. M.; Wei, S.; Tsogoeva, S. B. Org. Biomol. Chem. 2011, 9, 3457.

    Article  PubMed  Google Scholar 

  23. Gao, X.; Pan, Y. M.; Lin, M.; Chen, L.; Zhan, Z. P. Org. Biomol. Chem. 2010, 8, 3259.

    Article  CAS  PubMed  Google Scholar 

  24. Al-Hourani, B. J.; Banert, K.; Gomaa, N.; Vrobel, K. Tetrahedron 2008, 64, 5590.

    Article  Google Scholar 

  25. Sheldrake, P. W.; Matteucci, M.; McDonald, E. Synlett 2006, 460.

  26. Zhang, G.; Chen, B.; Guo, X.; Guo, S.; Yu, Y. Adv. Synth. Catal. 2015, 357, 1065.

    Article  CAS  Google Scholar 

  27. Chen, B.; Guo, S.; Guo, X.; Zhang, G.; Yu, Y. Org. Lett. 2015, 17, 4698.

    Article  CAS  PubMed  Google Scholar 

  28. Karamthulla, S.; Pal, S.; Khan, M. N.; Choudhury, L. H. RSC Adv. 2014, 4, 37889.

    Article  CAS  Google Scholar 

  29. Saroha, M.; Khurana, J. M. New J. Chem. 2019, 43, 8644.

    Article  CAS  Google Scholar 

  30. Mousavizadeh, F.; Talebizadeh, M.; Anary-Abbasinejad, M. Tetrahedron Lett. 2018, 59, 2970.

    Article  CAS  Google Scholar 

  31. Anary-Abbasinejad, M.; Nezhad-Shahrokhabadi, F.; Mohammadi, M. Mol. Diversity 2020, 24, 1205.

    Article  Google Scholar 

  32. Dehghanzadeh, F.; Shahrokhabadi, F.; Anary-Abbasinejad, M. ARKIVOC 2019, (v), 133.

  33. Riley, H. A.; Gray, A. R. Organic Synthesis; Wiley: New York, 1943, vol. 2, p. 509.

  34. Khalid, M.; Jawaria, R.; Khan, M. U.; Braga, A. A. C.; Shafiq, Z.; Imran, M.; Zafar, H. M. A.; Irfan, A. ACS Omega 2021, 6, 16058.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

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Correspondence to Mohammad Anary-Abbasinejad.

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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2023, 59(9/10), 709–712

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Latifi, M., Anary-Abbasinejad, M. & Mohammadi, M. A simple route for the synthesis of substituted thiazole derivatives by multicomponent reaction between arylglyoxals, acetylacetone or ethyl acetoacetate, and thiosemicarbazones. Chem Heterocycl Comp 59, 709–712 (2023). https://doi.org/10.1007/s10593-023-03258-z

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  • DOI: https://doi.org/10.1007/s10593-023-03258-z

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