Borax: An ecofriendly and efficient catalyst for one-pot synthesis of 3,4-dihydropyrimidine-2(1h)-ones under solvent-free conditions

Synthetic Communications

Volumn 40, Issue 20, 2010, Pages 2976-2982

  Nath, Jayashree ^a   Chaudhuri, Mihir K ^a,b  

^a INDIAN INSTITUTE OF TECHNOLOGY GUWAHATI   (India)

^b TEZPUR UNIVERSITY   (India)

Author keywords

3,4 dihydropyrimidin 2(1H) ones; Biginelli reaction; borax; solvent free

Indexed keywords

3,4 DIHYDROPYRIMIDIN 2(1H) ONE DERIVATIVE; 3,4 DIHYDROPYRIMIDINE 2(1H) THIONE DERIVATIVE; BORATE SODIUM; PYRIMIDINE DERIVATIVE; SOLVENT; SULFURIC ACID; THIOUREA; UNCLASSIFIED DRUG; UREA; VOLATILE ORGANIC COMPOUND;

ARTICLE; BIGINELLI REACTION; CATALYST; ECOSYSTEM; ONE POT SYNTHESIS; POLYMERIZATION; QUANTUM YIELD; REACTION ANALYSIS; REACTION TIME;

EID: 77956934821     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910903341163     Document Type: Article

References (30)

1. Yadav, J. S.; Reddy, B. V. S.; Reddy, K. B.; Raj, K. S.; Prasad, A. R. Ultrasound-accelerated synthesis of 3,4-dihydropyrimidin-2(1H)-ones with ceric ammonium nitrate. J. Chem. Soc., Perkin Trans. 2001, 1, 1939-1941.
2. Nandurkar, N. S.; Bhanushali, M. J.; Bhor, M. D.; Bhanage, B. M. Y(NO3)3- 6H2O: 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.
3. Paraskar, A. S.; Dewker, G. K.; 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.
4. Lu, J.; Bai, Y.; Wang, Z.; Yang, B.; Ma, H. One-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones using lanthanum chloride as a catalyst. Tetrahedron Lett. 2000, 41, 9075-9078.
5. 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, 2657-2659.
6. Su, W.; Li, J.; Zheng, Z.; Shen, Y. One-pot synthesis of dihydropyrimidiones catalyzed by strontium(II) triflate under solvent-free conditions. Tetrahedron Lett. 2005, 46, 6037-6040.
7. Ghose, R.; Maiti, S.; Chakraborty, A. In(OTf)3-catalysed one-pot synthesis of 3,4- dihydropyrimidin-2(lH)-ones. J. Mol. Catal. A: Chem. 2004, 217, 47-50.
8. Sun, Q.; Wang, Y.; Ge, Z.; Cheng, T.; Li, R. A highly efficient solvent-free synthesis of dihydropyrimidinones catalyzed by zinc chloride. Synthesis 2004, 1047-1051.
9. Lu, J.; Ma, H. Iron(III)-catalyzed synthesis of dihydropyrimidinones: Improved conditions for the Biginelli reaction. Synlett 2000, 63-64.
10. De, S. K.; Gibbs, R. A. Ruthenium(III) chloride-catalyzed one-pot synthesis of 3,4-dihydropyrimidin-2-(1H)-ones under solvent-free conditions. Synthesis 2005, 1748-1750.
11. Marby, 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.
12. Adib, M.; Ghanbary, K.; Mostofi, M.; Ganjali, M. R. Efficient Ce(NO3)3- 6H2O-catalyzed solvent-free synthesis of 3,4-dihydropyrimidin-2(1H)-ones. Molecules 2006, 11, 649-654.
13. Kalita, H. R.; Phukan, P. CuI as reusable catalyst for the Biginelli reaction. Catal. Commun. 2007, 8, 179-182.
14. Peng, J.; Deng, Y. Ionic liquids-catalyzed Biginelli reaction under solvent-free conditions. Tetrahedron Lett. 2001, 42, 5917-5919.
15. 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 solventless Biginelli condensation protocol. Synthesis 1999, 1799 - 1803.
16. Zhang, X.; Li, Y.; Liu, C.; Wang, J. An efficient synthesis of 4-substituted pyrazolyl-3,4- dihydropyrimidin-2(1H)-(thio)ones catalyzed by Mg(ClO4)2 under ultrasound irradiation. J. Mol. Catal. A: Chem. 2006, 253, 207-210.
17. Wipf, P.; Cunningham, A. A solid-phase protocol of the Biginelli dihydropyrimidine synthesis suitable for combinatorial chemistry. Tetrahedron Lett. 1995, 36, 7819-7822.
18. 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, 7975-7978.
19. Hu, E. H.; Sidler, D. R.; Dolling, U. H. Unprecedented catalytic three-component one-pot condensation reaction: An efficient synthesis of 5-alkoxycarbonyl-4-aryl- 3,4-dihydropyrimidin-2(1H)-ones. J. Org. Chem. 1998, 63, 3454-3457.
20. Tu, S.; Fang, F.; Miao, C.; Jiang, H.; Feng, Y.; Shi, D.; Wang, X. One-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones using boric acid as catalyst. Tetrahedron Lett. 2003, 44, 6153-6155.
21. Abdelmadjid, D.; Boudjemaa, B.; Mouna, A.; Ali, B.; Salah, R.; Bertrand, C. Phenylboronic acid as a mild and efficient catalyst for Biginelli reaction. Tetrahedron Lett. 2006, 47, 5697-5699.
22. Munoz-Muniz, O.; Juaristi, E. An enantioselective approach to the Biginelli dihydropyrimidinone condensation reaction using CeCl3 and InCl3 in the presence of chiral ligands. Arkivoc 2003, 9, 16-26.
23. Huang, Y.; Yang, F.; Zhu, C. Highly enantioseletive Biginelli reaction using a new chiral ytterbium catalyst: Asymmetric synthesis of dihydropyrimidines. J. Am. Chem. Soc. 2005, 127, 16386-16387.
24. Hussain, S.; Bharadwaj, S. K.; Chaudhuri, M. K.; Kalita, H. Borax as an efficient metal-free catalyst for hetero-Michael reactions in an aqueous medium. Eur. J. Org. Chem. 2007, 374-378.
25. Lu, J.; Bai, Y. J. Catalysis of the Biginelli reaction by ferric and nickel chloride hexahydrates: One-pot synthesis of 3,4-dihydropyrimidin-2(1H)- ones. Synthesis 2002, 4, 466-470.
26. Peyman, S.; Minoo, D.; Mohammad, A. Z.; Mohammad, A. B. F. 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.
27. Franz, L. Z.; Melanie, F.; Krischan, S.; Andreas, L. Propane phosphonic acid anhydride: A new promoter for the one-pot Biginelli synthesis of 3,4-dihydropyrimidin-2(1H)-ones. Tetrahedron Lett. 2007, 48, 1421-1423.
28. Heravi, M. M.; Derikvand, F. F.; Bamoharram, F. A catalytic method for synthesis of Biginelli-type 3,4-dihydropyrimidin-2 (1H)-one using 12-tungstophosphoric acid. J. Mol. Catal. A: Chem. 2005, 242, 173-175.
29. Badaoui, H. E.; Bazi, R.; Tahir, R.; Lazrek, H. B.; Sebti, S. Synthesis of 3,4-dihydropyrimidin-2-ones catalysed by fluorapatite doped with metal halides. Catal. Commun. 2005, 6, 455-458.
30. Tajbakhsh, M.; Mohajerani, B.; Heravi, M. M.; Ahmedi, A. N. Natural HEU type zeolite-catalyzed Biginelli reaction for the synthesis of 3,4-dihydropyrimidin-2(1H) one derivatives. J. Mol. Catal. A: Chem. 2005, 236, 216-219.