One-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones using CuBr2 as catalyst

Preparative Biochemistry and Biotechnology

Volumn 36, Issue 4, 2006, Pages 375-381

  Zhou, Haixia ^a   He, Miao ^a   Liu, Chunsheng ^a   Jiang, Heng ^a   Luo, Genxiang ^a  

^a LIAONING SHIHUA UNIVERSITY   (China)

Author keywords

Biginelli reaction; Catalyst; CuBr2; Dihydropyrimidinones; One pot; Synthesis

Indexed keywords

ALCOHOL; BROMIDE; COPPER; CUPRIC BROMIDE; PYRIMIDINONE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMISTRY; SYNTHESIS;

BROMIDES; CATALYSIS; COPPER; ETHANOL; PYRIMIDINONES;

EID: 33748684342     PISSN: 10826068     EISSN: 15322297     Source Type: Journal    
DOI: 10.1080/10826060600912682     Document Type: Article

References (16)

1. Kappe, C.O. 100 years of the Biginelli dihydropyrimidine synthesis. Tetrahedron 1993, 49 (32), 6937-6963.
2. Atwal, K.S.; Swanson, B.N.; Unger, S.E. Dihydropyrimidine calcium channel blockers: 3-carbamoyl-4-aryl-1,2,3,4-tetrahydro-6-methyl-5-pyrimidine carboxylic acid esters as orally effecitive antihypertensive agent. J. Med. Chem. 1991, 34 (2), 806-811.
3. Kappe, C.O.; Fabian, W.M.F. Conformational analysis of 4-aryl-dihydropyrimidine calcium channel modulators: A compareson of ab initio, semiempirical and X-ray crystallographic studies. Tetrahedron 1997, 53 (8), 2803-2816.
4. Snider, B.B.; Chen, J.; Patil, A.D.; Freyer, A. Synthesis of the tricyclic portions of batzelladines A, B and D. Revision of the stereochemistry of batzelladines A and D. Tetrahedron Lett. 1996, 37 (39), 6977-6980.
5. Folkers, K.; Harwood, H.J.; Johnson, T.B. Researches on pyrimidines.cxxx. synthesis of 2-keto-1,2,3,4-tetrahydropymidines. J. Am. Chem. Soc. 1932, 54 (9), 3751-3758.
6. 2: a reusable catalyst for high-yield synthesis of 3,4-dihydropyrimidin-2(1H)-ones. Tetrahedron Lett. 2003, 44 (16), 3305-3308.
7. Yarapathi, R.V.; Kurva, S.; Tammishetti, S. Synthesis of 3,4-dihydropyrimidin-2(1H)ones using reusable poly(4-vinylpyridineAco- divinylbenzene)-Cu(II)complex. Catal. Comm. 2004, 5 (9), 511-513.
8. 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, 2004 (2), 235-238.
9. Salehi, H.; Guo, Q.-X. A facile and efficient one-pot synthesis of dihydropyrimidinones catalyzed by magnesium bromide under solvent-free conditions. Synth. Comm. 2004, 34 (1), 171-179.
10. Gohain, M.; Prajapati, D.; Sandhub, S.J. A novel Cu-catalysed three-component one-pot synthesis of dihydropyrimidin-2(1H)-ones using microwaves under solvent-free conditions. Synlett. 2004, 2004 (2), 0235-0238.
11. 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, 2004 (7), 1047-1051.
12. Tu, S.J.; Fang, F.; Zhu, S.L.; Li, T.J.; Zhang, X.J.; Zhuang, Q. A new Biginelli reaction procedure using potassium hydrogen sulfate as the promoter for an efficient synthesis of 3,4-dihydropyrimidin-2(1H)-one. Synlett. 2004, (3), 537-539.
13. Ramalinga, K.; Vijayalakshmi, P.; Kaimal, T.N.B. Bismuth(III)-catalyzed synthesis of dihydropyrimidinones: improved protocol conditions for the Biginelli reaction. Synlett. 2001, 2001 (6), 863-865.
14. 3H under ultrasound irradiation. Ultrason. Sonochem 2003, 10 (3), 119-122.
15. Ahmad, S.B.; Ayoob, B.; Fatemeh, T. Ammonium chloride-catalyzed one-pot synthesis of 3,4-dihydropyrimidin-2-(1H)-ones under solvent-free conditions. Tetrahedron Lett. 2003, 44 (16), 857-859.
16. 20 catalyzed Biginelli reaction. one-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones. Chinese. J. Chem. 2002, 20 (7), 681-687.