One-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones catalyzed by acidic ionic liquids under solvent-free conditions

Synthetic Communications

Volumn 39, Issue 19, 2009, Pages 3436-3443

  Gui, Jianzhou ^a   Liu, Dan ^a   Wang, Chan ^a   Lu, Feng ^a   Lian, Jingzhao ^a   Jiang, Heng ^a   Sun, Zhaolin ^a  

^a LIAONING SHIHUA UNIVERSITY   (China)

Author keywords

Acidic ionic liquid; Biginelli reaction; Synthesis

Indexed keywords

3,4 DIHYDROPYRIMIDIN 2(1H)ONE; 5 ACETO 4,6 DIMETHYL 3,4 DIHYDROPYRIMIDIN 2 (1H)ONE; 5 ACETO 6 METHYL 4 (2,4 DICHLOROPHENYL) 3,4 DIHYDROPYRIMIDINE 2(1H)ONE; 5 ACETO 6 METHYL 4 (4 NITROPHENYL) 3,4 DIHYDROPYRIMIDIN 2 (1H)ONE; 5 ACETO 6 METHYL 4 ETHYL 3,4 DIHYDROPYRIMIDIN 2 (1H)ONE; 5 ETHOXYCARBONYL 6 METHYL 4 PROPYL 3,4 DIHYDROPYRIMIDIN 2 (1H)ONE; 5 METHOXYCARBONYL 4,6 DIMETHYL 3,4 DIHYDROPYRIMIDIN 2 (1H)ONE; 5 METHOXYCARBONYL 6 METHYL 4 (4 HYDROXY 3 METHOXYPHENYL) 3,4 DIHYDROPYRIMIDIN 2(1H)ONE; ALDEHYDE; CARBONYL DERIVATIVE; IONIC LIQUID; PYRIMIDINE DERIVATIVE; SOLVENT; UNCLASSIFIED DRUG; UREA;

ACIDITY; ARTICLE; BIGINELLI REACTION; CATALYSIS; CATALYST; ONE POT SYNTHESIS;

EID: 70349221562     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910902774042     Document Type: Article

References (25)

1. Romanelli, G. P.; Sathicq, A. G.; Autino, J. C.; Baronetti, G.; Thomas, H. J. Solvent-free approach to 3,4-dihydropyrimidin-2(1H)-(thio)ones: Biginelli reaction catalyzed by a Wells-Dawson reusable heteropolyacid. Synth. Commun. 2007, 37 (22), 3907-3916.
2. Xu, F.; Wang, J.; Tian, Y. New procedure for one-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones by Biginelli reaction. Synth. Commun. 2008, 38 (8), 1299-1310.
3. Mabry, J.; Ganem, B. Studies on the Biginelli reaction: A mild and selective route to 3,4-dihydropyrimidin-2(1H)-ones via enamine intermediates. Tetrahedron Lett. 2006, 47, 55-56.
4. Wang, M.; Song, Z.; Gong, H. Praseodymium methanesulfonate-catalyzed one-pot synthesis of 3,4-dihydropyrimidin-2-(1H)-ones. Prep. Bio. Biotech. 2008, 38 (1), 105-114.
5. Yu, Y.; Liu, D.; Liu, C; Luo, G. One-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones using chloroacetic acid as catalyst. Biol. Med. Chem. Lett. 2007,17, 3508-3510.
6. Gui, J.; Deng, Y.; Hu, Z.; Sun, Z. A novel task-specific ionic liquid for Beckmann rearrangement: A simple and effective way for product separation. Tetrahedron Lett. 2004, 45, 2681-2683
7. Gui, J.; Cong, X.; Liu, D.; Zhang, X.; Hu, Z.; Sun, Z. Novel Brønsted acidic ionic liquid as efficient and reusable catalyst system for esterification. Catal. Commun. 2004, 5, 473
8. Gui, J.; Ban, H.; Cong, X.; Zhang, X.; Hu, Z.; Sun, Z. Selective alkylation of phenol with tert-butyl alcohol catalyzed by Brønsted acidic imidazolium salts. J. Mol. Catal. A 2004, 225, 27
9. Gui, J.; Liu, D.; Cong, X.; Zhang, X.; Jiang, H.; Hu, Z.; Sun, Z. Clean synthesis of adipic acid by direct oxidation of cyclohex-ene with H2O2 catalyzed by Na2WO4 ■ 2H2O and acidic ionic liquid. J. Chem. Res. 2005, 520-522
10. Gui, J.; Liu, D.; Sun, Z. Cyclotrimerization of aliphatic aldehyde catalyzed by acidic ionic liquid. React. Kinet. Catal. Lett. 2007, 90, 35-43.
11. Li, M.; Guo, W.; Wen, L.; Li, Y.; Yang, H. One-pot synthesis of Biginelli and Hantzsch products catalyzed by non-toxic ionic liquid (BMImSac) and structural determination of two products. J. Mol. Catal. A: Chem. 2006, 2589 (1-2), 133-138
12. Zheng, R.; Wang, X.; Xu, H.; Du, J. Brønsted acidic ionic liquid: An efficient and reusable catalyst for the synthesis of 3,4-dihydropyrimidin- 2(1H)-ones. Synth. Commun. 2006, 36 (11), 1503-1513
13. Fang, D.; Luo, J.; Zhou, X.; Ye, Z.; Liu, Z. One-pot green procedure for Biginelli reaction catalyzed by novel task-specific room-temperature ionic liquids. J. Mol. Catal. A: Chem. 2007, 274, 208-211.
14. Liu, D.; Gui, J.; Zhu, X.; Song, L.; Sun, Z. Synthesis and characterization of task-specific ionic liquids possessing two Brønsted acid sites. Synth. Commun. 2007, 37, 759-765.
15. Xu, H.; Wang, Y. One-pot construction 3,4-dihydropyrimidin-2-(1H)-ones catalysed by samarium(III). J. Chem. Res. 2003, 377-379.
16. 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-(1H)-ones. Tetrahedron Lett. 2003, 44, 2889-2891.
17. Tu, S.; Fang, F.; Miao, C; Jiang, H.; Feng, Y.; Shi, D. One-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones using boric acid as catalyst. Tetrahendron Lett. 2003, 44, 6153-6153
18. Reddy, C. V.; Mahesh, M.; Raju, P. V. K.; Babu, T. R.; Reddy, V. V. N. Zireohium (IV) chloride-catalyzed one-pot synthesis of 3,4-dihydropyrimidin- 2(1H)-ones. Tetrahedron Lett. 2002, 43, 2657-2659.
19. Kappe, C. O. A reexamination of the mechanism of the Biginelli dihydropyr-imidine synthesis: Support for an N-acyliminium ion intermediate. J. Org. Chem. 1997, 62, 7201-7203.
20. Kappe, C. O.; Kumar, D.; Varma, R. S. Microwave-assisted high-speed parallel synthesis of 4-aryl-3,4-dihydropyrimidin-2-(1H)-ones using a solvent-less Biginelli condensation protocol. Synthesis 1999, 10, 1799-1803.
21. 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-(1H)-ones. Tetrahedron Lett. 2003, 44, 2889-2891.
22. Yadav, J. S.; Reddy, B. V. S.; Reddy, K. B.; Raj, K. S.; Prassad, A. R. Ultrasound-accelerated synthesis of 3,4-dihydropyrimidin-2(1H)-ones with ceric ammonium nitrate. J. Chem. Soc., Perkin Trans. 1, 2001, 1934-1937.
23. Tu, S.; Jiang, H.; Fang, F.; Zhuang, Q.; Miao, C.; Xu, F.; Shi, D.; Wang, X. Synthesis of 4-aryl-5-ethoxylcarbonyl-6-methyl-3,4-dihydropyrid-2-one under solvent-free conditions and microwave irradiation. Chin. J. Struct. Chem. 2003, 22 (5), 617-619. (Pubitemid 37260130)
24. Yarim, M.; Sarac, S.; Ertan, M. Synthesis, structural elucidation, and pharmacological properties of some 5-acetyl-3,4-dihydro-6-methyl-4-(substituted phenyl)-2-(1H)-pyrimidinones. Farmaco 1999, 54, 359-363.
25. Wang, M.; Jiang, H.; Wang, Z. Biginelli condensation of aliphatic aldehydes catalysed by zinc methanesulfonate. J. Chem. Res. 2005, 691-693.