Xanthan sulfuric acid: A new and efficient biosupported solid acid catalyst for the synthesis of 3,4-dihydropyrimidin-2(1H)-ones

Synthetic Communications

Volumn 42, Issue 8, 2012, Pages 1211-1217

  Kuarm, B Suresh ^a   Madhav, J Venu ^a   Laxmi, S Vijaya ^a   Rajitha, B ^a  

^a NATIONAL INSTITUTE OF TECHNOLOGY   (India)

Author keywords

3,4 dihydropyrimidin 2(1H) ones; Biginelli reaction; One pot synthesis; Solvent free conditions

Indexed keywords

3,4 DIHYDROPYRIMIDIN 2(1H) ONE DERIVATIVE; 5 (ETHOXYCARBONYL) 6 METHYL 4 PHENYL 3,4 DIHYDROPYRIMIDIN 2(1H) ONE; ALDEHYDE; AMINE; ETHYL 1,2,3,4 TETRAHYDRO 4 (7 HYDROXY 2 OXO 2H CHROMEN 8 YL) 6 METHYL 2 THIOXOPYRIMIDINE 5 CARBOXYLIC ACID; ETHYL 1,2,3,4 TETRAHYDRO 6 METHYL 2 OXO 4 (4 OXO 4H CHROMEN 3 YL)PYRIMIDINE 5 CARBOXYLIC ACID; ETHYL 1,2,3,4 TETRAHYDRO 6 METHYL 4 (6 NITRO 4 OXO 4H CHROMEN 3 YL) 2 OXOPYRIMIDINE 5 CARBOXYLIC ACID; ETHYL 1,2,3,4 TETRAHYDRO 6 METHYL 4 (NAPHTHALEN 6 YL) 2 THIOXOPYRIMIDINE 5 CARBOXYLIC ACID; PYRIMIDINONE DERIVATIVE; SOLVENT; SULFURIC ACID; THIOUREA; UNCLASSIFIED DRUG; UREA; XANTHAN; XANTHAN SULFURIC ACID;

ARTICLE; CATALYST; CATALYST SUPPORT; DRUG SYNTHESIS; INFRARED SPECTROSCOPY; ONE POT SYNTHESIS; POLYMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION TIME; SOLVENT EFFECT; THIN LAYER CHROMATOGRAPHY;

EID: 84857614494     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397911.2010.538483     Document Type: Article

References (32)

1. Kochi, M. Green Reaction Media for Organic Synthesis; Blackwell: Oxford, 2005.
2. Kappe, C. O. One hundred years of the Biginelli dihydropyrimidine synthesis. Tetrahedron 1993, 49, 6937.
3. Kappe, C. O.; Shishkin, O. V.; Uray, G.; Verdino, P. X-ray structure, conformational analysis, enantioseperation, and determination of absolute configuration of the mitotic kinesin Eg5 inhibitor monastrol. Tetrahedron 2000, 56, 1859.
4. (a) Kappe, C. O. Biologically active dihydropyrimidones of the Biginellitype: A literature survey. Eur. J. Med. Chem. 2000, 35, 1043-1052; (Pubitemid 32050011)
5. (b) Patil, A. D.; Kumar, N. V.; Kokke, W. C.; Bean, M. F.; Freyer, A. J.; C. De, Brosse; Mai, S.; Truneh, A.; Faulkner, D. J.; Carte, B.; Breen, A. L.; Hertzberg, R. P.; Johnson, R. K.; Westley, J. W.; Potts, B. C. Novel alkaloids from the sponge Batzella sp.: Inhibitors of HIV gp120-human CD4 binding. J. Org. Chem. 1995, 60, 1182-1188.
6. Snider B., B.; Shi, Z. Biomimetic synthesis of (±)-crambines A, B, C1, and C2: Revision of the structure of crambines B and C1. J. Org. Chem. 1993, 58, 3828-3839.
7. Biginelli, P. Aldehyde-urea derivatives of aceto- and oxaloacetic acids. Gazz. Chim. Ital. 1893, 23, 360.
8. Folkers, K.; Harwood, H. J.; Johnson, T. B. Research on pyrimidines, 130: Synthesis of 2-keto-1,2,3,4-tetrahydropyrimidines. J. Am. Chem. Soc. 1932, 54, 3751.
9. Hu, E. H.; Sidler, D. R.; Dolling, U. H. Unprecedented catalytic three-component onepot condensation reaction: An efficient synthesis of 5-alkoxycarbonyl-4-aryl-3, 4-dihydropyrimidin-2(1H)-ones. J. Org. Chem. 1998, 63, 3454.
10. Kappe, C. O.; Falsone, S. F. Polyphosphate Ester-mediated synthesis of dihydropyrimidinones: Improved conditions for the Biginelli reaction. Synlett 1998, 718.
11. Bigi, F.; Carloni, S.; Frullanti, B.; Maggi, R.; Sartori, G. A revision of the Biginelli reaction under solid acid catalyst: Solvent-free synthesis of dihydropyrimidinones over montmorillonite KSF. Tetrahedron Lett. 1999, 40, 3465.
12. 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.
13. 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.
14. Bussolari, J. C.; McDonnell, P. A. A new substrate for the Biginelli cyclocondensation: Direct preparation of 5-unsubstituted 3,4-dihydropyrimidin- 2(1H)-ones from a b-keto carboxylic acid. J. Org. Chem. 2000, 65, 6777.
15. Dondoni, A.; Massi, A. Parallel synthesis of dihydropyrimidinones using Yb(III)-resin and polymer-supported scavengers under solvent-free conditions: A green chemistry approach to the Biginelli reaction. Tetrahedron Lett. 2001, 42, 7975.
16. Peng, J.; Deng, Y. Ionic liquid-catalyzed Biginelli reaction under solvent free conditions. Tetrahedron Lett. 2001, 42, 5917.
17. Ramalinga, K.; Vijayalakshmi, P.; Kaimal, T. N. B. Bismuth(III)-catalyzed synthesis of dihydropyrimidinones: Improved protocol conditions for the Biginelli reaction. Synlett 2001, 6, 863.
18. 4-catalyzed one-pot synthesis of dihydropyrimidinones. Synthesis 2001, 1341.
19. Fu, N. Y.; Yuan, Y. F.; Cao, Z.; Wang, S. W.; Wang, J. T.; Peppe, C. Indium (III) bromide-catalyzed preparation of dihydropyrimidinones: Improved protocol conditions for the Biginelli reaction. Tetrahedron 2002, 58, 4801.
20. 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.
21. Reddy, C. V.; Mahesh, M.; Raju, P. V. K.; Babu, T. R.; Reddy, V. V. N. Zirconium(IV) chloride-catalyzed one-pot synthesis of 3,4 dihydropyrimidin-2(1H) -ones. Tetrahedron Lett. 2002, 43, 2657.
22. Prabhakar, A. S.; Dewkar; Sudalai, A. Cu(OTf)2: A reusable catalyst for high-yield synthesis of 3,4 dihydropyrimidin-2(1H)-ones. Tetrahedron Lett. 2003, 44, 3305-3308. (Pubitemid 36369455)
23. Srisnivas Rao, A.; Ravivarala; Mujahid Alam, M. Bismuth triflate-catalyzed one-pot synthesis of 3,4-dihydropyrimidin-2(1H) ones: An improved protocol for the Biginelli reaction. Synlett 2003, 1, 67.
24. Wang, L.; Qian, C.; Tian, He.; Yun, M. A. Lanthanide triflate-catalyzed one-pot synthesis of dihydropyrimidin-2(1H)-thiones by a three-component of 1,3-dicarbonyl compounds, aldehydes, and thiourea using a solvent-free Biginelli condensation. Synth. Commun. 2003, 33, 1459-1468. (Pubitemid 36547546)
25. 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.
26. Sargent, E. V.; Adolph, J.; Clemmons, M. K.; Kirk, G. D.; Pena, B. M.; Fedoruk, M. J. Evaluation of flu-like symptoms in workers handling xanthan gum powder. J. Occup. Med. 1990, 32, 625.
27. Davidson, R. L. (Ed.). Handbook of Water-Soluble Gums and Resins; McGraw-Hill: New York, 1980.
28. Whistler, R. L.; BeMiller, J. N. (Eds.). Industrial Gums: Polysaccharides and Their Derivatives; Academic Press: San Diego, 1973.
29. (a) Naveen Kumar, V.; Sunil Kumar, B.; Narsimha Reddy, P.; Thirupathi Reddy, Y.; Rajitha, B. Selectfluor-catalyzd one-pot synthesis of dihydropyrimidinones: An improved protocol for the Biginelli reaction. Heterocycl. Commun. 2007, 13, 29-32;
30. (b) Rao, G. V. P.; Thirupathi Reddy, Y.; Narasimha Reddy, P.; Rajitha, B. Bismuth oxide perchlorate- catalysed efficient synthesis of 3,4-difydro pyrimidine-2-(1H)-ones: An improved highyielding protocol for the Biginelli reaction. Ind. J. Chem. 2005, 44B, 2378;
31. (c) Rao, G. V. P.; Thirupathi Reddy, Y.; Narasimha Reddy, P.; Rajitha, B. Bismuth subnitrate- catalysed efficient synthesis of 3,4-dihydropyrimidine-2- (1H)-ones: An improved protocol for the Biginelli reaction. Synth. Commun. 2004, 34, 3821.
32. Shaabani, A.; Maleki, A.; Soudi, M. R.; Mofakham, H. Xanthan sulfuric acid: A new and efficient bio-supported solid acid catalyst for the synthesis of a-amino nitriles by condensation of carbonyl compounds, amines, and trimethylsilylcyanide. Catal. Commun. 2009, 10, 945.