Preparation of 1,5-Diketones by Addition of Cyclohexanone to Chalcones under Solvent-free Phase Transfer Catalyst Condition

Eight different chalcone-1,5-diketone derivatives (5a-h) were prepared by the reaction of chalcone derivatives (3a-h) with cyclohexanone under the solvent-free phase transfer catalyst condition with modarate to high yields. The mechanistic pathway of the reaction can be explained by the Michael-type addition of cyclohexanone to chalcone derivatives (3a-h).

Preparation of 1,5-Diketones by Addition of Cyclohexanone to Chalcones under Solvent-free Phase Transfer Catalyst Condition

Eight different chalcone-1,5-diketone derivatives (5a-h) were prepared by the reaction of chalcone derivatives (3a-h) with cyclohexanone under the solvent-free phase transfer catalyst condition with modarate to high yields. The mechanistic pathway of the reaction can be explained by the Michael-type addition of cyclohexanone to chalcone derivatives (3a-h).

___

  • M. Satyanarayana, P. Tiwari, B. K. Tripathi, A. K. Sriwastava, R. Pratap, Bioorg. Med. Chem., 12, 883, (2004).
  • S. Mukherjee, N. Kumar, A. K. Parasad, H. G. Raj, M. E. Bracke, C. E. Olsen, S. C. Jain, V. S. Parmar, Bioorg. Med. Chem., 9, 337 (2001).
  • H. K. Hsieh, L. T. Tsao, J. P. Wang, C. N. Lin, J. Pharm. Pharmacol., 52, 163 (2000).
  • V. J. Ram, A. S. Saxena, S. Srivastava, S. Chandra, Bioorg. Med. Chem. Lett., 10, 2159 (2000).
  • L. Zhai, M. Chen, J. Blam, T. G. Theander, S. B. Chiristensen, A. Kharazmi, J. Antimicrob. Chemother., (1999).
  • R. J. Anto, K. Sukumuran, G. Kuttan, M. N. A. Rao, V. Subbaraju, R. Kuttan, Cancer Lett., 97, 33 (1995).
  • S. K. Kumar, E. Hager, P. Catherine, H. Gurulingappa, N. E. Davidson, S. R. Khan, J. Med. Chem., 46, (2003).
  • Z. S. Arigan, H. Suschitiky, J. Chem. Soc., 2242 (1961).
  • F. Krohnke, Synthesis, 1, (1976).
  • E. C. Constable, A. M. W. Cargill, J. Chem. Soc. Dalton Trans., 2947 (1992).
  • I. R. Butler, S. J. Mcdonald, Polyhedron, 14, 529 (1995).
  • B. S. Goud, K. Panneerselvam, D. E. Zacharis, G. R. Desiraju, J. Chem. Soc.Perkin Trans., 2, 325 (1995).
  • X. L. Li, Y. M. Wang, T. Matsuura, J. B. Meng, J. Heterocyc. Chem., 36, 697 (1999).
  • W. Y. Liu, Q. H. Xu, Y. M. Liang, B. H. Chen, W. M. Liu, Y. X. Ma, J. Organomet. Chem., 637-639, 719 (2001).
  • A. Hoz, E. D. Barra, F. Langa, S. Merino, A. Rodriguez, P. S. Verdu, Tetrahedron, 53, 34, 11693 (1997).
  • A. G. Raso, J. G. Raso, B. Campaner, R. Mestres, J. V. Sinisterra, Comunications, 1037 (1982).
  • S. Wattanasin, W. S. Murphy, Synthesis, 647 (1980).
  • D. G. Powers, D. S. Casebier, D. Fokas, W. J. Ryan, J. R. Troth, D. L. Coffen, Tetrahedron, 54, 4085 (1998).
  • Y. Sasson, M. Cohen, J. Blum, Communucations, 359, (1973).
  • D. G. Batt, R. Goodman, D. G. Jones, J. S. Kerr, L. R. Mantegna, C. McAllister, R. C. Newton, S. Nurnberg, P. K. Welch, M. B. Covington, J. Med. Chem., 36, 1434 (1993).
  • O. V. Singh, C. P. Garg, R. P. Kapoor, Synthesis, 1025 (1990).
  • E. J. Corey, F. Y. Zhang, Org. Lett., 1, 1287 (1999).
  • F. Y. Zhang, E. J. Corey, Org. Lett., 2, 1097 (2000).
  • N. H. Num, Y. Kim, Y. J. You, D. H. Hong, H. M. Kim, B. Z. Ahn, Eur. J. Med. Chem., 38, 179 (2003).
  • Y. Hu, X. Liang , J. Wang , Z. Zheng , X. Hu, J. Org. Chem., 68, 4542 (2003).
  • S. Harada, N. Kumagai, T. Kinoshita, S. Matsunaga, M. Shibasaki, J. Am. Chem. Soc., 125, 2582 (2003).
  • A. Puschl, H. C. Rudbeck, A. Faldt, A. Confante, J. Kehler, Synthesis, 291 (2005).
  • J. Wang, H. Li, L. Zu, W. Wang, Adv. Synth. Catal., 425 (2006).
  • T. G. Nikolaeva, N. V. Petrova, A. P. Kriven’ko, Chem. Heterocycl. Comp., 35, 813 (1999).
Turkish Journal of Chemistry-Cover
  • ISSN: 1300-0527
  • Yayın Aralığı: Yılda 6 Sayı
  • Yayıncı: TÜBİTAK