One-pot synthesis of fused 3,4-dihydropyrimidin-2(1 H )-ones and thiones using a novel ionic liquid as an efficient and reusable catalyst: Improved protocol conditions for the Biginelli-like scaffolds

Heterocyclic Communications

Volumn 18, Issue 2, 2012, Pages 93-97

  Janardhan, Banothu ^a   Laxmi, Somarapu Vijaya ^a   Rajitha, Bavanthu ^a  

^a NATIONAL INSTITUTE OF TECHNOLOGY   (India)

Author keywords

4 dihydropyrimidin 2(1H) ones; Fused 3; Novel ionic liquid with multi SO 3H groups; One pot synthesis; Solvent free conditions; Thiones

Indexed keywords

EID: 84862585247     PISSN: 07930283     EISSN: None     Source Type: Journal    
DOI: 10.1515/hc-2011-0109     Document Type: Article

References (19)

1. Akshay, M. P.; Mahesh, M. S.; Chirag, V. B.; Naval, K.; Jyoti, S.; Yogesh, T. N. An efficient, environment friendly and recyclable heterogeneous catalyst for the Biginelli condensation. Lett. Org. Chem. 2009 , 6 , 619-623.
2. Atwal, K. S.; Rovnyak, G. C.; O'Reilly, B. C.; Schwartz, J. Synthesis of selectively functionalized 2-hetero-1, 4 dihydropyrimidines. J. Org. Chem. 1989 , 54 , 5898-5907.
3. 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.
4. Bao, S.; Chen, L.; Ji, Y.; Yang, J. Efficient procedure for oxathioacetalization using the novel ionic liquid. Chin. J. Chem. 2010 , 28 , 2119-2122.
5. Bimal, K. B.; Anupama, T. R.; Arup, D.; Chhanda, M. Microwaveinduced bismuth nitrate-catalyzed synthesis of dihydropyrimidones via Biginelli condensation under solventless conditions. Tetrahedron Lett. 2007 , 48 , 7392-7394.
6. Cheng, J.; Qi, D. Y. An efficient and solvent-free one-pot synthesis of dihydropyrimidinones under microwave irradiation. Chin. Chem. Lett. 2007 , 18 , 647-650.
7. Debache, A.; Amimour, M.; Belfaitah, A.; Rhouati, S.; Carboni, B. A one-pot Biginelli synthesis of 3, 4-dihydropyrimidin-2-(1 H )- ones/thiones catalyzed by triphenylphosphine as Lewis base. Tetrahedron Lett. 2008 , 49 , 6119-6121.
8. Dennis, R.; Fabrício, A. L.; Victor, S. S. D. S.; Karen, F. S. C.; Marcelo, G. M. D.; Marla, N. G. Multicomponent Biginelli's synthesis of 3, 4-dihydropyrimidin-2(1 H )-ones promoted by SnCl 2·2H 2O. J. Braz. Chem. Soc. 2004 , 15 , 165-169.
9. El-Baih, F. E. M.; Al-Rasheed, H. H.; Al-Hazimi, H. M. Synthesis of some pyridine and pyrimidine derivatives via Michael-addition. J. Saudi Chem. Soc. 2005 , 9 , 575-596.
10. Fabio, S. F.; Kappe, C. O. The Biginelli dihydropyrimidone synthesis using polyphosphate ester as a mild and efficient cyclocondensation/ dehydration reagent. Arkivoc 2001 , (ii) , 122-134.
11. Haixia, L.; Jinchang, D.; Xianten, C.; Ziyi, Z. An efficient synthesis of 5-alkoxycarbonyl-4-aryl-3, 4-dihydropyrimidin-2(1H)-ones catalyzed by KSF montmorillonite. Molecules 2000 , 5 , 1240-1243.
12. Ji-Tai, L.; Jun-Fen, H.; Jin-Hui, Y.; Tong-Shuang, L. An efficient synthesis of 3, 4-dihydropyrimidin-2-ones catalyzed by NH 2 SO 3 H under ultrasound irradiation. Ultrason. Sonochem. 2003 , 10 , 119-122.
13. Kamaljit, S.; Kawaljit, S.; Baojie, W.; Scott, F.; Kelly, C.; Jan, B. Facile transformation of Biginelli pyrimidin-2(1 H )-ones to pyrimidines. In vitro evaluation as inhibitors of Mycobacterium tuberculosis and modulators of cytostatic activity. Eur. J. Med. Chem. 2011 , 46 , 2290-2294.
14. Kumar, K. A.; Kasthuraiah, M.; Reddy, C. S.; Reddy, C. D. Mn(OAc) 3·2H 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.
15. 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.
16. Naveen Kumar, V.; Someshwar, P.; Narsimha Reddy, P.; Thirupathi Reddy, Y.; Rajitha, B. Copper dipyridine dichloride as a mild and efficient catalyst for a one-pot condensation Biginelli reaction. J. Heterocycl. Chem. 2005 , 42 , 1-3.
17. Peng, J. J.; Deng, Y. Q. Ionic liquids catalyzed Biginelli reaction under solvent-free conditions. Tetrahedron Lett. 2001 , 42 , 5917-5919.
18. Rahim, H.; Maryam, H.; Majid, M. H.; Bita, B. Efficient sodium selenate-catalyzed synthesis of 3, 4-dihydro-2(1 H )-pyrimidinones and thiones under solvent-free conditions. Bull. Chem. Soc. Ethiop. 2009 , 23 , 141-144.
19. Salehi, P.; Dabiri, M.; Zolfigol, M. A.; Fard, M. A. B. Silica sulfuric acid: an efficient and reusable catalyst for the one-pot synthesis of 3, 4-dihydropyrimidin-2(1 H )-ones. Tetrahedron Lett. 2003 , 44 , 2889-2891.