Copper (II) sulfamate: An efficient catalyst for the one-pot synthesis of 3,4-dihydropyrimidine-2(1H)-ones and thiones

Molecules

Volumn 14, Issue 2, 2009, Pages 763-770

  Liu, Chen Jiang ^a,b   Wang, Ji De ^a,b  

^a XI'AN JIAOTONG UNIVERSITY   (China)

^b XINJIANG UNIVERSITY   (China)

Author keywords

Biginelli reaction; Copper(II) sulfamate; Dihydropyrimidinones

Indexed keywords

ACETIC ACID DERIVATIVE; ALDEHYDE; COPPER; PYRIMIDINONE DERIVATIVE; SULFAMIC ACID; SULFONIC ACID DERIVATIVE; THIOKETONE; UREA;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

ACETATES; ALDEHYDES; CATALYSIS; COPPER; MOLECULAR STRUCTURE; PYRIMIDINONES; SULFONIC ACIDS; THIONES; UREA;

EID: 61449251574     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules14020763     Document Type: Article

References (29)

1. Kappe, C.O. 100 Years of the Biginelli dihydropyridine synthesis. Tetrahedron 1993, 49, 6937-6963.
2. Kappe, C.O.; Fabian, W.M.F.; Semones, M.A. Conformational Analysis of 4-Aryl-Dihydropyrimidine Calcium Channel Modulators. A Comparison of Ab Initio, Semiempirical and X-Ray Crystallography Studies. Tetrahedron 1997, 53, 2803-2816.
3. Kappe, C.O. Recent Advances in the Biginelli Dihydropyrimidine Synthesis. New Tricks from an Old Dog. Ace. Chem. Res. 2000, 33, 879-888.
4. Atwal, K. S.; Rovnyak, G. C.; Kimball, S. D.; Floyd,D. M.; Moreland, S.; Swanson, B. N.; Gougoutas, D. Z.; Schewartz, J.; Smillie, K. M.; Malley, M. F. Dihydropyrimidine Calcium Channel Blockers. II. 3-Substituted-4-aryl-1,4- dihydro-6-methyl-5-pyrimidinecarboxylic Acid Esters as Potent Mimics of Dihydropyridines. J. Med. Chem. 1990, 33, 2629-2635
5. Nagarathnam, D.; Miao, S.W.; Lagu, B.; Chiu, G.; Fang, J.; Murali Dhar, T.G.; Zhang, J.; Tyagarajan, S.; Marzabadi, M.R.; Zhang, F.; Wong, W.C.; Sun, W.; Tian, D.; Zhang, J.; Wetzel, J.M.; Forray, C.; Chang, R.S.L.; Broten, T.P.; Schorn, T.W.; Chen, T.B.; O'Malley, S.; Ransom, R.W.; Schneck, K.; Bendesky, R.; Harrell, C.M.; Gluchowski, C. Design and Synthesis of Novel au Adrenoceptor-Selective Antagonists. 1. Structure-Activity Relationship in Dihydropyrimidinones. J. Med. Chem. 1999, 42, 4764-4777.
6. Patil, A.D.; Kumar, N.V.; Kokke, W.C; Bean, M.F.; Freyer, A.J.; Brossi, C.D.; Mai, S.; Truneh, A.; Faulkner, D.J.; Carte, B.; Breen, A.L.; Hertzberg, R.P.; Johnson, R.K.; Westly, J.W.; Potts, B.C.M.; Novel Alkaloids from the Sponge Batzella sp.: Inhibitors of HIV gp120-Human CD4 Binding. J. Org. Chem. 1995, 60, 1182-1188.
7. Snider, B.B.; Chen, J.; Patil, A.D.; Freyer, A. Synthesis of the Tricyclic Portions of Batzelladines A, B and D. Revision of the Stereoehemistry of Batzelladines A and D. Tetrahedron Lett. 1996, 37, 6977-6980.
8. Biginelli, P. Gazz. Chim. Ital. 1893, 23, 360-413.
9. Banik, B.K.; Reddy, A.T.; Datta A.; Mukhopadhyay C. Microwave-induced Bismuth NitrateCatalyzed Synthesis of Dihydropyrimidones via Biginelli Condensation under Solventless Conditions. Tetrahedron Lett. 2007, 48, 7392-7394.
10. 3H under Ultrasound Irradiation. Ultrason. Sonochem. 2003, 10, 119-122.
11. Peng, J.J.; Deng, Y.Q. Ionic Liquids Catalyzed Biginelli Reaction under Solvent-free Conditions. Tetrahedron Lett. 2001, 42, 5917-5919.
12. 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.
13. Tu, S.J.; Fang, F.; Miao, C.B.; Jiang, H.; Feng, Y.J.; Shi, D.Q.; Wang, X.S.; One-Pot Synthesis of 3,4-Dihydropyrimidin-2(1H)-ones Using Boric Acid as Catalyst. Tetrahedron Lett. 2003, 44, 6153-6155.
14. Sabitha, G.; Reddy, G.S.K.K.; Reddy, K.B.; Yadav, J.S. Vanadium(III) Chloride Catalyzed Biginelli Condensation: Solution Phase Library Generation of Dihydropyrimidin-(2H)-ones. Tetrahedron Lett. 2003, 44, 6497-6499.
15. Su, W.K.; Li, JJ.; Zheng, Z.G.; Shen, Y.C. One-pot Synthesis of Dihydropyrimidiones Catalyzed by Strontium(II) triflate under Solvent-free Conditions. Tetrahedron Lett. 2005, 46, 6037-6040.
16. Debache, A.; Amimour, M.; Belfaitah, A.; Rhouati, S.; Carboni, B. A One-Pot Biginelli Synthesis of 3,4-Dihydropyrimidin-2-(1H)-ones/thiones Catalyzed by Triphenylphosphine as Lewis Base. Tetrahedron Lett. 2008, 49, 6119-6121.
17. Fu, N.Y.; Yuan, Y.F.; Pang, M.L.; Wang, J.T.; Peppe, C. Indium(III) Halides-Catalyzed Preparation of Ferrocenedihydropyrimidinones. J. Organomet. Chem. 2003, 672, 52-57.
18. 2O Support ed on Silica Gel as a Novel Heterogeneous System Catalyzed Biginelli Reaction One-Pot Synthesis of Di-hydropyrimidinones under Solvent-free Conditions. Appl. Catal. A Gen. 2006, 300, 85-88.
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(1H)-ones. Tetrahedron Lett. 2003, 44, 2889-2891.
20. H2O- 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.
21. 2O: A Novel and Reusable Catalyst for One Pot Synthesis of 3,4-Dihydropyrimidin-2(1H)-ones under Solvent-free Conditions. J. Mol. Catal. A Chem. 2007, 271, 14-17.
22. Ghosh, R.; Maiti, S.; Chakraborty, A. In(OTf)3-Catalysed One-Pot Synthesis of 3,4-Dihydropyrimidin-2(1H)-ones. J. Mol. Catal. A Chem. 2004, 277, 47-50.
23. 5-Catalyzed Biginelli Reaction: One-Pot Synthesis of 3,4-Dihydropyrimidin-2-(177)-ones/thiones under Solvent-Free Conditions. Tetrahedron Lett. 2007, 48, 5407-5409.
24. 2O-Catalyzed Solvent -Free Synthesis of 3,4-Dihydropyrimidin-2(1H)-ones. Molecules 2006, 11, 649-654.
25. Karade, H.N.; Sathe, M.; Kaushik, M.P. Synthesis of 4-Aryl Substituted 3,4-Di hydropyrimidinones Using Silica-chloride Under Solvent Free Conditions. Molecules 2001, 12, 1341-1351.
26. 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.
27. Liu, C.J.; Wang, J.D.; Li, Y.P. One-Pot Sythesis of 3,4-Dihydropyrimidin- 2(lH)-ones Using Strontium(II) Nitrate as a Catalyst. J. Mol. Catal. A Chem. 2006, 258, 367-370.
28. Zhang, X.L.; Li, Y.P.; Liu, C.J.; Wang, J.D. An Efficient Synthesis of 4-Substituted pyrazolyl3,4-dihydropyrimidin-2(177)-(thio)ones Catalyzed by Mg(C1O4)2 under Ultrasound Irradiation. J. Mol. Catal. A Chem. 2006, 253, 207-211.
29. Kappe, C.O. A Reexamination of the Mechanism of the Biginelli Dihydropyrimidine Synthesis. Support for an N-Acyliminium Ion Intermediate. J. Org. Chem. 1997, 62, 7201-7204.