Synthesis of 4-phenyl-3,4-tetrahydro-indeno [2,1]-pyrimidin-2-one (LR-1)

Ritmaleni Ritmaleni, Wahyu Nurcahyani


The synthetic compound 4-phenyl-3,4-tetrahydro-indeno[2,1]- pyrimidin-2-one 20a (LR-1) was synthesised using Biginelli reaction method. The reaction involved benzaldehyde 6, 2-indanone 2 and urea 7 in acid condition. This condensation reaction yielded 15 % of the product 20, at 133,4-135,0oC of melting point and 0.15 (Et2O : CHCl3 = 1 : 3) of Rf  value.

Keywords : benzaldehyde, indenone-2, urea

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Atwal, K. S., Swanson, B. N., Unger, S. E., Floyd, D. M., Moreland, S., Hedberg, A., and O'Reilly, B. C. ,1991, 3-Carbamoyl-4-aryl-1,2,3,4-tetrahydro-6-methyl-5-pyrimidinecarboxylic Acid Esters as Orally Effective Antihypertensive Agents. J. Med. Chem. 34, 806

Dolle, R. E., and Nelson, K. H., 1999, Comprehensive Survey of Combinatorial Library Synthesis J. Comb. Chem. 1, 235

Domling, A., 2002, Curr. Opin. Chem. Biol. 6, 306, cit., Bose, D. S., Sudharshan, M., Chavhan, S. W., 2005, New Protocol for Biginelli Reaction-a Practical Synthesis of Monastrol, Arkivoc, 3, 587

Gordon, E. M., Gallop, M. A., and Patel, D. V., 1996, Strategy and Tactics in Combinatorial Organic Synthesis. Applications to Drug Discovery, Acc. Chem. Res. 29, 144.

Hurst, E. W., and Hull, R., 1961, J. Med. Pharm. Chem. 3, 215.

Jauk, B., Pernat, T., and Kappe, C. O., 2000, Design and Synthesis of a Conformationally Rigid Mimic ... Calcium Channel Modulator SQ32,926, Molecules 5, 227.

Kape, C. O., 1998, 4-Aryldihydropyrimidines via Biginelli Condensations: Aza Analogs of Nifedipine-Type Calcium Channel Modulators, Molecules 3, 1.

Kappe, C. O.,1993, 100 Years of The Biginelli Dihydropyrimidine Synthesis, Tetrahedron 49, 6937

Kappe, C. O., 2000, Recent Advances in the Biginelli Dihydropyrimidine Synthesis. New. Tricks From an Old Dog, Acc. Chem. Res. 33, 879.

Kato, T.: Jpn. Kokay Koho 59 190,974: (CA 102:132067), 1984.

Mayer, T. U., Kapoor, T. M., Haggarty, S. J., King, R. W., Schreiber, S. I., and Mitchison, T. J., 1999, Small Molecule Inhibitor of Mitotic Spindle Bipolarity Indetified in a Phenotype- Based Screen, Science 286, 971.

Patil, A. D., kumar, N. V., Kokke, W. C., Bean, M. F., Freyer, A. J., Debrossi, C., Mai, S., Truneh, A., Fraulkner, D. J., Carte, B., Breen, A. L., Hertzberg, R. P., Johnson, R. K., Westley, J. W., and Potts, B. C. M., 1995 Novel Alkaloids from the Sponge Batzella sp.: Inhibitors of HIV gp 120-human CD4 Binding, J. Org. Chem. 60, 1182.

Rovnyak, G. C., Atwal, K. S., Hedberg, A., Kimball, S. D., Moreland, S., Gougoutas, J. Z., O'Reilly, B. C., Schwartz, J., and Malley, M. F., 1992, Basic 3-Substituted-4-aryl-1,4- dihydropyrimidine-5-carboxylic Acid Esters. Potent Antihypertensive Agents, J. Med. Chem. 35, 3254, 1992.

Russowsky, D., Lopes, F. A., Da Silva, V. S. S., Canto, K. F. S., D'Oca, M. G. M., and Godoi, M. N., 2004, Multicomponent Biginelli's Synthesis of 3,4-dihydropyrimidin-2(1H)-ones Promoted by SnCl2.2H2O, J. Braz. Chem. soc. 15, 2.

Thompson, L. A., and Ellman, J. A., 1996, Synthesis and Applications of Small Molecule Libraries, Chem. Rev. 96, 555.

Weber, L., 2002, Multicomponent Biginelli's synthesis of 3,4-dihydropyrimidin-2-(1H)-ones promoted by SnCl2.2H2O. Drug. Disc. Today 7, 143.



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