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).

Kaynakça

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).

Kaynak Göster

Bibtex @ { tbtkchem142418, journal = {Turkish Journal of Chemistry}, issn = {1300-0527}, eissn = {1303-6130}, address = {}, publisher = {TÜBİTAK}, year = {2008}, volume = {32}, pages = {55 - 61}, doi = {}, title = {Preparation of 1,5-Diketones by Addition of Cyclohexanone to Chalcones under Solvent-free Phase Transfer Catalyst Condition}, key = {cite}, author = {Ceylan, Mustafa and Gezegen, Hayreddin} }
APA Ceylan, M , Gezegen, H . (2008). Preparation of 1,5-Diketones by Addition of Cyclohexanone to Chalcones under Solvent-free Phase Transfer Catalyst Condition . Turkish Journal of Chemistry , 32 (1) , 55-61 .
MLA Ceylan, M , Gezegen, H . "Preparation of 1,5-Diketones by Addition of Cyclohexanone to Chalcones under Solvent-free Phase Transfer Catalyst Condition" . Turkish Journal of Chemistry 32 (2008 ): 55-61 <
Chicago Ceylan, M , Gezegen, H . "Preparation of 1,5-Diketones by Addition of Cyclohexanone to Chalcones under Solvent-free Phase Transfer Catalyst Condition". Turkish Journal of Chemistry 32 (2008 ): 55-61
RIS TY - JOUR T1 - Preparation of 1,5-Diketones by Addition of Cyclohexanone to Chalcones under Solvent-free Phase Transfer Catalyst Condition AU - Mustafa Ceylan , Hayreddin Gezegen Y1 - 2008 PY - 2008 N1 - DO - T2 - Turkish Journal of Chemistry JF - Journal JO - JOR SP - 55 EP - 61 VL - 32 IS - 1 SN - 1300-0527-1303-6130 M3 - UR - Y2 - 2021 ER -
EndNote %0 Turkish Journal of Chemistry Preparation of 1,5-Diketones by Addition of Cyclohexanone to Chalcones under Solvent-free Phase Transfer Catalyst Condition %A Mustafa Ceylan , Hayreddin Gezegen %T Preparation of 1,5-Diketones by Addition of Cyclohexanone to Chalcones under Solvent-free Phase Transfer Catalyst Condition %D 2008 %J Turkish Journal of Chemistry %P 1300-0527-1303-6130 %V 32 %N 1 %R %U
ISNAD Ceylan, Mustafa , Gezegen, Hayreddin . "Preparation of 1,5-Diketones by Addition of Cyclohexanone to Chalcones under Solvent-free Phase Transfer Catalyst Condition". Turkish Journal of Chemistry 32 / 1 (Ocak 2008): 55-61 .
AMA Ceylan M , Gezegen H . Preparation of 1,5-Diketones by Addition of Cyclohexanone to Chalcones under Solvent-free Phase Transfer Catalyst Condition. Turk J Chem. 2008; 32(1): 55-61.
Vancouver Ceylan M , Gezegen H . Preparation of 1,5-Diketones by Addition of Cyclohexanone to Chalcones under Solvent-free Phase Transfer Catalyst Condition. Turkish Journal of Chemistry. 2008; 32(1): 55-61.
IEEE M. Ceylan ve H. Gezegen , "Preparation of 1,5-Diketones by Addition of Cyclohexanone to Chalcones under Solvent-free Phase Transfer Catalyst Condition", Turkish Journal of Chemistry, c. 32, sayı. 1, ss. 55-61, Oca. 2008