Cellulose sulfuric acid: An efficient biodegradable and recyclable solid acid catalyst for the one-pot synthesis of 3,4-dihydropyrimidine-2(1H)-ones

Synthetic Communications

Volumn 39, Issue 7, 2009, Pages 1257-1263

  Reddy, P Narsimha ^a   Reddy, Y Thirupathi ^a   Reddy, M Nikhil ^a   Rajitha, B ^a   Crooks, Peter A ^a  

^a University of Kentucky   (United States)

Author keywords

3,4 dihydropyrimidin 2(1H) ones; Biginelli reaction; Biosupported catalyst; Cellulose sulfuric acid (CSA); One pot synthesis

Indexed keywords

3,4 DIHYDROPYRIMIDINE 2(1H) ONE DERIVATIVE; CELLULOSE SULFURIC ACID; PYRIMIDINONE DERIVATIVE; SULFURIC ACID; UNCLASSIFIED DRUG;

ARTICLE; BIODEGRADATION; CATALYSIS; DRUG STRUCTURE; ONE POT SYNTHESIS; POLYMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 61949366035     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910802517871     Document Type: Article

References (37)

1. Atwal, K. S.; Swanson, B. N.; Unger, S. E.; Floyd, D. M.; Moreland, S.; Hedberg, A.; O'Reilly, B. C. Dihydropyrimidine calcium channel blockers, 3: 3-Carbamoyl-4-aryl-1,2,3,4-tetrahydro-6-methyl-5-pyrimidinecarboxylic acid esters as orally effective antihypertensive agents. J. Med. Chem. 1991, 34, 806-811.
2. Rovnyak, G. C.; Atwal, K. S.; Hedberg, A.; Kimball, S. D.; Moreland, S.; Gougoutas, J. Z.; O'Reilly, B. C.; Schwart, J.; Malley, M. F. Dihydropyrimidine calcium channel blockers, 4: Basic 3-substituted-4-aryl-1,4-dihydropyrimidine-5- carboxylic acid esters: Potent antihypertensive agents. J. Med. Chem. 1992, 35, 3254-3263.
3. Grover, G. J.; Dzwonczyk, S.; Mcmullen, D. M.; Normadinam, C. S.; Slenph, P. G.; Moreland, S. J. Pharmacologic profile of the dihydropyrimidine calcium channel blockers SQ 32,547 and SQ 32,926. J. Cardiovasc. Pharmacol. 1995, 26, 289-294.
4. Ghorab, M. M.; Abdel-Gawad, S. M.; El-Gaby, M. S. A. Synthesis and evaluation of some new fluorinated hydroquinazoline derivatives as antifungal agents. Farmaco 2000, 55, 249-255.
5. Shivarama Holla, B.; Sooryanarayana Rao, B.; Sarojini, B. K.; Akberali, P. M. One pot synthesis of thiazolodihydropyrimidinones and evaluation of their anticancer activity. Eur. J. Med. Chem. 2004, 39, 777-783.
6. Delia, T. J.; Baumann, M.; Bunker, A. Fused pyrimidines, V: Pyrimido[4,5-d] pyrimidine analogues of folic acid. Heterocycles 1993, 35, 1397-1409.
7. Kappe, C. O. Biologically active dihydropyrimidones of the Biginelli-type - A literature survey. Eur. J. Med. Chem. 2000, 35, 1043-1052.
8. Lu, J.; Bai, Y. Catalysis of the Biginelli reaction by ferric and nickel chloride hexahydrates: One-Pot synthesis of 3,4-dihydropyrimidin-2(1H)- ones. Synthesis 2002, 4, 466-470.
9. Gohain, M.; Prajapati, D.; Sandhu, J. S. A novel Cu-catalysed three-component one-pot synthesis of dihydropyrimidin-2(1H)-ones using microwaves under solvent-free conditions. Synlett 2004, 2, 235-238.
10. Bose, D. S.; Fatima, L.; Mereyala, H. B. 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. 2003, 68, 587-590.
11. 2O-mediated three-component, one-pot, condensation reaction: An efficient synthesis of 4-aryl-substituted 3,4-dihydropyrimidin-2-ones. Tetrahedron Lett. 2001, 42, 7873-7875.
12. Reddy, C. V.; Mahesh, M.; Raju, P. V. K.; Ramesh Babu, T.; Narayana Reddy, V. V. Zirconium(IV) chloride catalyzed one-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones. Tetrahedron Lett. 2002, 43, 2657-2659.
13. Ranu, B. C.; Hajra, A.; Jana, U. Indium(III) chloride-catalyzed one-pot synthesis of dihydropyrimidinones by a three-component coupling of 1,3-dicarbonyl compounds, aldehydes, and urea: An improved procedure for the Biginelli reaction. J. Org. Chem. 2000, 65, 6270-6272.
14. Sun, Q.; Wang, Y.-Q.; Ge, Z.-M.; Cheng, T.-M.; Li, R.-T. A highly efficient solvent-free synthesis of dihydropyrimidinones catalyzed by zinc chloride. Synthesis 2004, 7, 1047-1051.
15. Ramaliga, K.; Vijayalakshmi, P.; Kaimal, T. N. B. Bismuth(III)-catalyzed synthesis of dihydropyrimidinones: Improved protocol conditions for the Biginelli reaction. Synlett 2001, 6, 863-865.
16. Khodaei, M. M.; Salehi, P.; Zolfigol, M. A.; Sirouszadeh, S. Efficient synthesis of 3,4-dihydropyrimidin-2-(1H)-ones by aluminum hydrogensulfate. Pol. J. Chem. 2004, 78, 385-388.
17. Varala, R.; Alam, M. M.; Adapa, S. R. Bismuth triflate catalyzed one-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones: An improved protocol for the Biginelli reaction. Synlett 2003, 1, 67-70.
18. Bose, D. S.; Kumar, R. K.; Fatima, L. A remarkable rate acceleration of the one-pot three-component cyclocondensation reaction at room temperature: An expedient synthesis of mitotic kinesin eg5 inhibitor monastrol. Synlett 2004, 2, 279-282.
19. Debache, A.; Boumoud, B.; Amimour, M.; Belfaitah, A.; Rhouati, S.; Carboni, B. Phenylboronic acid as a mild and efficient catalyst for Biginelli reaction. Tetrahedron Lett. 2006, 47, 5697-5699.
20. Suzuki, I.; Suzumura, Y.; Takeda, K. Metal triflimide as a Lewis acid catalyst for Biginelli reactions in water. Tetrahedron Lett. 2006, 47, 7861-7864.
21. Maiti, G.; Kundu, P.; Guin, C. One-pot synthesis of dihydropyrimidinones catalyzed by lithium bromide: An improved procedure for the Biginelli reaction. Tetrahedron Lett. 2003, 44, 2757-2758.
22. Shaabani, A.; Bazgir, A.; Teimouri, F. Ammonium chloride-catalyzed one-pot synthesis of 3,4-dihydropyrimidin-2-(1H)-ones under solvent-free conditions. Tetrahedron Lett. 2003, 44, 857-859.
23. 2-catalyzed three-component, one-pot, condensation reaction: An efficient synthesis of 4-aryl-5-substituted- 6-methyl-3,4-dihydropyrimidin-2(1H)-ones. Indian J. Chem., Sect. B 2003, 42, 2604-2607.
24. 4-catalyzed one-pot synthesis of dihydropyrimidinones: An improved protocol for Biginelli reaction. Synthesis 2001, 9, 1341-1345.
25. Ivica, C.; Mladen, L.; Mirela, F.-L.; Ivana, G. Antimony(III) chloride catalyzed Biginelli reaction: A versatile method for the synthesis of dihydropyrimidinones through a different reaction mechanism. Tetrahedron 2007, 63, 11822-11827.
26. Hu, E. H.; Silder, D. R.; Dolling, U. H. Unprecedented catalytic three component one-pot condensation reaction: An efficient synthesis of 5-alkoxy carbonyl-4-aryl-3,4-dihydropyrimidin-2(1H)-ones. J. Org. Chem. 1998, 63, 3454-3457.
27. Ma, Y.; Qian, C.; Wang, L.; Yang, M. Lanthanide triflate catalyzed Biginelli reaction. one-pot synthesis of dihydropyrimidinones under solvent-free conditions. J. Org. Chem. 2000, 65, 3864-3868.
28. Dondoni, A.; Mossi, A.; Minghini, E.; Sabbatini, S.; Bertolosi, V. Model studies toward the synthesis of dihydropyrimidinyl and pyridyl alpha-amino acids via three-component Biginelli and Hantzsch cyclocondensations. J. Org. Chem. 2003, 68, 6172-6183.
29. Joseph, J. K.; Jain, S. L.; Sain, B. Ion exchange resins as recyclable and heterogeneous solid acid catalysts for the Biginelli condensation: An improved protocol for the synthesis of 3,4-dihydropyrimidin-2-ones. J. Mol. Catal. A 2006, 247(1-2), 99-102.
30. Bigi, F.; Carloni, S.; Frullanti, B.; Maggi, R.; Sartori, G. A revision of the Biginelli reaction under solid acid catalysis. Solvent-free synthesis of dihydropyrimidines over montmorillonite KSF. Tetraheron Lett. 1999, 40, 3465-3468.
31. Radha Rani, V.; Srinivas, N.; Radha Kishan, M.; Kulkarni, S. J.; Raghavan, K. V. Zeolite-catalyzed cyclocondensation reaction for the selective synthesis of 3,4-dihydropyrimidin-2(1H)-ones. Green Chem. 2001, 3, 305-306.
32. Jin, T.; Zhang, S.; Guo, J.; Li, T. A simple and efficient synthesis of 3,4-dihydropyrimidin-2-ones catalysed by amidosulfonic acid. J. Chem. Res., Synop. 2002, 37-39.
33. Breslow, R. Biomimetic control of chemical selectivity. Acc. Chem. Res. 1980, 13, 170-177.
34. Clark, J. H.; Macquarrie, D. J. Green Chemistry and Technology; Blackwell: Abingdon, UK, 2002.
35. Ahmad, S.; Ali, M. Cellulose sulfuric acid as a bio-supported and recyclable solid acid catalyst for the one-pot three-component synthesis of a-amino nitriles. Appl. Catal. A. 2007, 331, 149-151.
36. Ahmad, S.; Ali, M.; Jafar, R.; Ebrahim, S. Cellulose sulfuric acid catalyzed one-pot three-component synthesis of imidazoazines. Chem. Pharm. Bull. 2007, 55(6), 957-958.
37. Ahmad, S.; Abbas, R.; Zahra, B. Sulfonated cellulose and starch: New biodegradable and renewable solid acid catalysts for efficient synthesis of quinolines. Catal. Comm. 2008, 9, 13-16.