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Stereoselective Crossed-Aldol Condensation of Hetarylmethyl Ketones with Aromatic Aldehydes in Water : Synthesis of (2E)-3-Aryl-1-hetarylprop-2-en-1-ones

  • Basaif, Salem A. (Chemistry Department, Faculty of Science, King Abdulaziz University) ;
  • Sobahi, Tatiq R. (Chemistry Department, Faculty of Science, King Abdulaziz University) ;
  • Khalil, Ali Kh. (Chemistry Department, Faculty of Science, Ain Shams University) ;
  • Hassan, Mohamed A. (Chemistry Department, Faculty of Science, Ain Shams University)
  • Published : 2005.11.20

Abstract

Aldol condensation of 2-acetylthiophene, 2-acetylpyrrole and 2-acetylpyridine with different aromatic aldehydes were carried out in water in heterogeneous phases in the presence of cetyltrimethylammonium bromide as cationic surfactant at room temperature. All the reactions occur in a short time with excellent yields of steroselective hetarylpropanones in water as environmental friendly solvent.

Keywords

References

  1. Dhar, D. N. Chemistry of Chalcones and Related Compounds; Wiley: N. Y., 198
  2. Wu, J. H.; Wang, X. H.; Yi, Y. H.; Lee, K. H. Bioor. & Med. Chem. Let. 2003, 13, 1813 https://doi.org/10.1016/S0960-894X(03)00197-5
  3. Nam, N. H.; Kim, Y.; You, Y. J.; Hong, D. H.; Kim, H. M.; Ahn, B. Z. Eur. J. Med. Chem. 2003, 38, 179 https://doi.org/10.1016/S0223-5234(02)01443-5
  4. Saydam, G.; Aydin, H. H.; Sahin, F.; Kucukoglu, O.; Erciyas, E.; Terzioglu, E.; Buyukkececi, F.; Omay, S. B. Leukemia Res. 2003, 27, 57 https://doi.org/10.1016/S0145-2126(02)00058-9
  5. Wu, X.; Wilairat, P.; Go, M. L. Bioorg. & Med. Chem. Let. 2002, 12, 2299 https://doi.org/10.1016/S0960-894X(02)00430-4
  6. Dominguez, J. N.; Charris, J. E.; Lobo, G.; Dominguez, N. G.; Moreno, M. M.; Riggione, F.; Sanchez, E.; Olson, J.; Rosenthal, P. J. Eur. J. Med. Chem. 2001, 36, 555 https://doi.org/10.1016/S0223-5234(01)01245-4
  7. Tuchinda, P.; Reutrakul, V.; Claeson, P.; Pongprayoon, U.; Sematong, T.; Santisuk, T.; Taylor, W. C. Phytochemistry 2002, 59, 169 https://doi.org/10.1016/S0031-9422(01)00451-4
  8. Herencia, F.; Ferrandiz, M. L.; Ubeda, A.; Dominguez, J. N.; Charris, J. E.; Lobo, G. M.; Alcaraz, M. J. Bioorg. & Med. Chem. Let. 1998, 8, 1169 https://doi.org/10.1016/S0960-894X(98)00179-6
  9. Xia, Y.; Yang, Z. Y.; Xia, P.; Bastow, K. F.; Nakanishi, Y.; Lee, K. H. Bioorg. & Med. Chem. Let. 2000, 10, 699 https://doi.org/10.1016/S0960-894X(00)00072-X
  10. Ducki, S.; Forrest, R.; Hadfield, J. A.; Kendall, A.; Lawrence, N. J.; McGown, A. T.; Rennison, D. Bioorg. & Med. Chem. Let. 1998, 8, 1051 https://doi.org/10.1016/S0960-894X(98)00162-0
  11. Li, C. J. Chem. Rev. 1993, 93, 2023 https://doi.org/10.1021/cr00022a004
  12. Reichardt, C. Solvent and Solvent Effects in Organic Chemistry, 2nd Ed.; VCH: 1988
  13. Breslow, R. Acc. Chem. Res. 1991, 24, 159 https://doi.org/10.1021/ar00006a001
  14. March, J. Advanced Organic Chemistry, 4th Ed.; Wiley: 1992
  15. Toda, F.; Tanaka, K.; Hamai, K. J. Chem. Soc. Perkin Trans. I 1990, 3207
  16. Nivalkar, K. R.; Mudaliar, C. D.; Mashraqui, S. H. J. Chem. Res. Synop. 1992, 98
  17. Fringuelli, F.; Pani, G.; Piermatti, O.; Pizzo, F. Tatrahedron 1994, 50, 11499 https://doi.org/10.1016/S0040-4020(01)89287-5
  18. Fringuelli, F.; Pani, G.; Piermatti, O.; Pizzo, F. Life Chem. Rep. 1995, 13, 133
  19. Zhang, Z.; Dong, Y.; Wang, G. Chem. Lett. 2003, 32(10), 966 https://doi.org/10.1246/cl.2003.966

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