Synthesis and Characterization of Some New Bis-(Dihydropyrimidinones-5-Carboxamide) by Using Ultrasonic Irradiation
DOI:
https://doi.org/10.23918/eajse.v3i3p132Keywords:
Dihydropyrimidinone, Biginelli Condensation, Ultrasonic, Hydrolysis, Catalytic ReactionAbstract
This investigation involves synthesis of two new series of bis-dihydropyrimidinone-5-carboxamides (4 a-k) and (5 a-k) from reaction of 6-methyl-2-oxo-4-phenyl-1,2,3,4-tetra-hydropyrimidine-5-carbonyl chloride and its derivatives (3 a, b) with different diamines using ultrasonic irradiation. Compounds (3a, b) were synthesized from chlorination of 6-methyl-2-oxo-4-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid and its derivatives (2a,b) which were prepared from hydrolysis of ethyl-6-methyl-2-oxo-4-phenyl-1,2,3,4-tetrahydropyrimi-dine-5-carbo-xylate and its derivatives (1a, b) which was synthesized by one-pot Biginelli condensation. The synthesized products were characterized by physico-chemical methods such as elemental analysis (CHNS-O), FT-IR, 1H-NMR and 13C-NMR. The prepared compounds were showed biological activity against two types of bacterial Escherichia coli Gram-negative bacteria (G -ve) and Staphylococcus aureas Gram-positive bacteria (G +ve).
References
Baruah, P., Gadhwal, S., Prajabati, D., & Sandhu, J. (2002). The biginelli condensation: A novel and
efficient regioselective synthesis of dihydropyrimidin-2(1h)-ones using lithium bromide.
Chemistry Letters, 31(10), 1038-1039.
Bose, D., Fatima, D., & Merelya, L. (2003). Green chemistry approaches to the synthesis of 5-
alkoxycarbonyl-4-aryl-3, 4- dihydropyrimidin-2(1h)-ones by a three-component coupling
of one-pot condensation reaction: comparison of ethanol, water, and solvent-free
conditions. J. Org. Chem., 68, 587-590.
Carlos, J., Bernardi, D., & Kirsch,G. (2007). ZrCl4 or ZrOCl2 under neat conditions: Optimized
green alternatives for the Biginelli reaction. Tetrahedron Letters, 48, 5777-5780.
Chen, W., Dong, S., & Jin, J.(2007). HBF4-catalyzed Biginelli reaction: One-pot synthesis of
dihydropyrimidin-2(1H)-ones under solvent-free conditions. Catalysis Communications, 8,
123-126.
Chitra, S., & Pandiarajan, K. (2009). Calcium fluoride: An efficient and reusable catalyst for the
synthesis of 3, 4-dihydropyrimidin-2(1H)-ones and their corresponding 2(1H) thione: An
improved high yielding protocol for the Biginelli reaction. Tetrahedron Letters, 50, 2222-
2224.
Dong, F., Jun, L., Xinli, Z., Zhiwen, Y., & Zuliang, L. (2007). One-pot green procedure for Biginelli
reaction catalyzed by novel task-specific room-temperature ionic liquids. Journal of
Molecular Catalysis A: Chemical, 274, 208-211.
Hattori, K., Kohchi, Y., Oikawa, N., Suda, H., Ura, M., & Ishikawa, T.(2003). Design and synthesis
of the tumor-activated prodrug of dihydropyrimidine dehydrogenase (DPD) inhibitor,
RO0094889 for combination therapy with capecitabine. Bioorganic & Medicinal
Chemistry Letters, 13,867-872.
Hu, E., Sidler, D., & Dolling, U. (1998). Unprecedented catalytic three component one-pot
condensation reaction: An efficient synthesis of 5-alkoxycarbonyl- 4-aryl-3, 4-
dihydropyrimidin-2(1H)-ones. J. Org. Chem., 63, 3454-3457.
Hurst, E., & Hull, R. (1961). Two new synthetic substances active against viruses of the psittacosislymphogranuloma-trachoma group. J. Med. Pharm. Chem., 3, 215-229.
Kappe, C. (2000). Biologically active dihydropyrimidones of the Biginelli-type — a literature
survey. Eur. J. Med. Chem., 35, 1043-1052.
Kashman,Y., Hirsh, S., McConnel, O., Ohtani, I., Takenori, K., & Kakisawa, H. (1989).
Ptilomycalin A: A novel polycyclic guanidine alkaloid of marine origin. J. Am. Chem. Soc.,
111, 8925-8926.
Khodabakhsh, N., Mohammad, A., & Nader, D. (2007). Efficient synthesis of 3, 4-
dihydropyrimidin-2 (1H)-one using metal hydrogen sulfates M (HSO4) n as catalyst under
solvent-free conditions. Chin. J. Catal., 28(7), 591-595.
Kim, J., & Jang, D. (2009). Mild and efficient cooper (ii) oxide-catalyzed acylation of amines and
alcohols. Bull. Korean Chem. Soc., 30, 1435-1436.
Lu, J., & Ma, H.(2000). Iron (III)-catalyzed synthesis of dihydropyrimidinones. Improved conditions
for the Biginelli reaction. Synlett, 1, 63-64.
Ma, Y., Qian, C., Wang, L., & Yang, M. (2000). Lanthanide triflate catalyzed biginelli reaction. onepot synthesis of dihydropyrimidinones under solvent-free conditions. J. Org. Chem., 65,
3864-3868.
Mayer, T., Kapoor, T., Haggarty, S., King, R., Schreiber, S., & Mitchison, T.(1999). Small molecule
inhibitor of mitotic spindle bipolarity identified in a phenotype-based screen. Science, 286,
971-974.
Mehta, T., Tahilramani, D., & Talwalker, T. (1971). Synthesis of some s-triazoles with potential
analgesic and antiinflammatory activities. J. Med. Chem., 14, 335-338.
Narsaiah, A., Basak, A., & Nagaiah, K. (2004). Cadmium chloride: An efficient catalyst for onepot synthesis of 3, 4‐dihydropyrimidin‐2‐ [1H] ‐ones. Synthesis, 8, 1253-1256.
Osnaya, R., Arroyo, G., Parada, L., Delgado, F., Trujillo, J., Salmón, M., & Miranda, R. (2003).
Biginelli vs Hantzsch esters study under infrared radiation and solventless conditions (MX870EP). Arkivoc, xi, 112-117.
Patil, A., Kumar, N., Kokke, W., Bean, M., Freyer, A., DeBrosse, C., Mai, S., Trunesh, A., Faulkner,
D., Carte, B., Breen, A., Hertzberg, R., Johnson, R., Westley, J., & Potts, B. (1995). Novel
Alkaloids from the Sponge Batzella sp.: Inhibitors of HIV gp120-Human CD4 Binding. J.
Org. Chem., 60, 1182-1188.
Rovnyak, G., Kimball, S., Cucinotta, G., Dimareo, J., Gougoutas, J., & Hedberg, A. (1995). Calcium
entry blockers and activators: Conformational and structural determinants of
dihydropyrimidine calcium channel modulators. J. Med. Chem., 38, 119-129.
Salehi, P., Dabiri, M., Zolfigol, M., & Fard, M. (2003). Silica sulfuric acid: An efficient and reusable
catalyst for the one-pot synthesis of 3, 4-dihydropyrimidin-2(1H)-ones. Tetrahedron Lett.,
44, 2889-2891.
Singh, K., Arora, D., Singh, K., & Singh, S. (2009). Genesis of dihydropyrimidinone calcium
channel blockers: Recent progress in structure-activity relationships and other effects.
Mini-Reviews in Medicinal Chemistry, 9, 95-106.
Snider, B., & Shi, Z. (1993). Biomimetic synthesis of (.+-.)-crambines A, B, C1, and C2: Revision of
the structure of crambines B and C1. J. Org. Chem., 58, 3828-3839.
Stadler, A., & Kappe, O. (2001). Automated library generation using sequential microwave-assisted
chemistry: Application toward the biginelli multicomponent condensation.
J. Comb. Chem., 3, 624-630.
Tawfik, H., Bassyouni, F., Gamal-Eldeen, A., & Abo-Zeid, M. (2009). Tumor anti-initiating activity
of some novel 3, 4-dihydropyrimidinones. Pharmacological Reports, 61, 1153-1162.
Zhidovinova, M., Fedorova, O., Rusinov, G., & Ovchinnikova, I.(2003). Sonochemical synthesis of
Biginelli compounds. Russian Chemical Bulletin, 52, 2527-2528.
Zhu, Y., Huang, S., Wan, J.,.Yan, I., & Pan, Y. (2006). Two Novel Diastereoselective ThreeComponent Reactions of Alkenes or 3, 4-Dihydro-(2H)-pyran with
Urea/Thiourea−Aldehyde Mixtures: [4 + 2] Cycloaddition vs Biginelli-Type Reaction.
Org. Lett., 8, 2599-2602.
Downloads
Published
Issue
Section
License
This work is licensed under a Creative Commons Attribution 4.0 International License.
Eurasian J. Sci. Eng is distributed under the terms of the Creative Commons Attribution License 4.0 (CC BY-4.0) https://creativecommons.org/licenses/by/4.0/
