Lewis acid-doped natural phosphate: New catalysts for the one-pot synthesis of 3,4-dihydropyrimdin-2(1H)-one

Synthetic Communications

Volumn 35, Issue 19, 2005, Pages 2561-2568

  El Badaoui, Hanane ^a   Bazi, Fathallaah ^a   Tamani, Soumia ^a   Boulaajaj, Saïd ^a   Zahouily, Mohamed ^b   Lazrek, Hassan B ^c   Sebti, Saïd ^a  

^a FACULTÉ DES SCIENCES BEN M SIK   (Morocco)

^b HASSAN II UNIVERSITY   (Morocco)

^c FACULTÉ DES SCIENCES SEMLALIA   (Morocco)

Author keywords

Biginelli reaction; Catalysis; Condensation; Pyrimidinones

Indexed keywords

3,4 DIHYDROPYRIMIDINE 2(1H) ONE; 4 (4 CHLOROPHENYL) 5 ETHOXYCARBONYL 6 METHYL 3,4 DIHYDROPYRIMIDIN 2(1H) ONE; 5 ETHOXYCARBONYL 4 (2 FURFURYL) 6 METHYL 3,4 DIHYDROPYRIMIDIN 2(1H) ONE; 5 ETHOXYCARBONYL 4 (3 METHOXYPHENYL) 6 METHYL 3,4 DIHYDROPYRIMIDIN 2(1H) ONE; 5 ETHOXYCARBONYL 4 (4 METHOXYPHENYL) 6 METHYL 3,4 DIHYDROPYRIMIDIN 2(1H) ONE; 5 ETHOXYCARBONYL 6 METHYL 4 (3 NITROPHENYL) 3,4 DIHYDROPYRIMIDIN 2(1H) ONE; 5 ETHOXYCARBONYL 6 METHYL 4 PHENYL 3,4 DIHYDROPYRIMIDIN 2(1H) ONE; ALDEHYDE; ESTER DERIVATIVE; HALIDE; LEWIS ACID; METAL; PHOSPHATE; PYRIMIDINONE DERIVATIVE; UNCLASSIFIED DRUG; UREA;

ARTICLE; BIGINELLI REACTION; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CATALYST; CRYSTALLIZATION; POLYMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION OPTIMIZATION; SYNTHESIS;

EID: 26044483802     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910500213963     Document Type: Article

References (27)

1. Kappe, C. O. 100 years of the Biginelli dihydropyrimidine synthesis. Tetrahedron 1993, 49 (32), 6937-6963 and references cited therein.
2. Kappe, C. O. Biologically active dihydropyrimidones of the Biginelli-type - a literature survey. Eur. J. Med. Chem. 2000, 35 (12), 1043-1052.
3. Biginilli, P. Aldehyde-urea derivatives of aceto- and oxaloacetic acids. Gazz. Chem. Ital. 1893, 23, 360-413.
4. 2O-mediated three-component, one-pot, condensation reaction: An efficient synthesis of 4-aryl-substituted 3,4-dihydropyrimidin-2- ones. Tetrahedron Lett. 2001, 42 (44), 7873-7875.
5. 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 (45), 7975-7978.
6. Mitra, A. K.; Banerjee, K. Clay-catalysed synthesis of dihydropyrimidinones under solvent-free conditions. Synlett 2003, 10, 1509-1511.
7. Reddy, C. V.; Mahesh, M.; Raju, P. V.; Babu, T. R.; Reddy, V. V. Zirconium(IV) chloride-catalyzed one-pot synthesis of 3,4-dihydropyrimidin-2(1H) -ones. Tetrahedron Lett. 2002, 43 (14), 2657-2659.
8. 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, 7, 1047-1051.
9. 40 as a novel, water-tolerant heteropolyacid for the synthesis of 3,4-dihydropyrimidinones. Eur. J. Org. Chem. 2004, 3, 552-557.
10. Narsaiah, A. V.; Basak, A. K.; Nagaiah, K. Cadmium chloride: an efficient catalyst for one-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones. Synthesis 2004, 8, 1253-1256.
11. 2O-LiCl as an inexpensive catalyst system. Synth. Commun. 2004, 34 (9), 1559-1564.
12. Tu, S.; Fang, F.; Zhu, S.; Li, T.; Zhang, X.; 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. J. Heterocyclic Chem. 2004, 41 (2), 253-258.
13. Tu, S.; Fang, F.; Zhu, S.; Li, T.; Zhang, X.; 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.
14. Gholap, A. R.; Venkatesan, K.; Daniel, T.; Lahoti, R. J.; Srinivasan, K. V. Ionic liquid-promoted novel and efficient one-pot synthesis of 3,4-dihydropyrimidin-2-(1H)-ones at ambient temperature under ultrasound irradiation. Green Chem. 2004, 6(3), 147-150.
15. 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, 2, 235-238.
16. Kappe, C. O.; Stadler, A. The Biginelli dihydropyrimidine synthesis. Org. React. 2004, 63, 1-116.
17. Sebti, S.; Solhy, A.; Tahir, R.; Smahi, A.; Boulaajaj, S.; Mayoral, J. A.; García, J. I.; Fraile, J. M.; Kossir, A.; Oumimoun, H. Application of natural phosphate modified with sodium nitrate in the synthesis of chalcones: A soft and clean method. J. Catal. 2003, 213 (1), 1-6.
18. Sebti, S.; Rhihil, A.; Saber, A.; Hanafi, N. Catalyse hétérogène de l'hydratation des nitriles en amides par le phosphate naturel dopé par KF, le phosphate trisodique. Tetrahedron Lett. 1996, 37 (36), 6555-6556.
19. Sebti, S.; Rhihil, A.; Saber, A.; Laghrissi, M.; Boulaajaj, S. Synthèse des α-hydroxyphosphonates sur des supports phosphatés en absence de solvant. Tetrahedron Lett. 1996, 37 (23), 3999-4000.
20. Sebti, S.; Smahi, A.; Solhy, A. Natural phosphate doped with potassium fluoride and modified with sodium nitrate: Efficient catalysts for the Knoevenagel condensation. Tetrahedron Lett. 2002, 43 (10), 1813-1815.
21. Fraile, J. M.; Garcia, J. I.; Mayoral, J. A.; Sebti, S.; Tahir, R. Modified natural phosphate: Easily accessible basic catalyst for the epoxidation of electron deficient alkenes. Green Chem. 2001, 3 (6), 271-274.
22. Macquarrie, D. J.; Nazih, R.; Sebti, S. KF/natural phosphate as an efficient catalyst for synthesis of 2-hydroxychalcones, flavanones. Green Chem. 2002, 4(1), 56-59.
23. Zahouily, M.; Bahlaouane, B.; Aadil, M.; Rayadh, A.; Sebti, S. Natural phosphate doped with potassium fluoride: Efficient catalyst for the construction of carbon-carbon bond. Org. Process Res. Dev. 2004, 8 (2), 275-278.
24. Sebti, S.; Rhihil, A.; Saber, A. Heterogeneous catalysis of the Friedel-Crafts alkylation by doped natural phosphate and tricalcium phosphate. Chem. Lett. 1996, 8, 721.
25. Lazrek, H. B.; Rochdi, A.; Kabbaj, Y.; Taourirte, M.; Sebti, S. Zinc chloride-doped natural phosphate as 1,3-dipolar cycloaddition catalysts. Synth. Commun. 1999, 28 (6), 1057-1063.
26. Rochdi, A.; Taourirte, M.; Redwane, N.; Sebti, S.; Engels, J. W.; Lazrek, H. B. Doped natural phosphate: A new and environmentally friendly catalyst in nucleoside synthesis. Nucleos. Nucleot. Nucl. 2003, 22 (5/8), 679-682.
27. Alahiane, A.; Rochdi, A.; Taourirte, M.; Redwane, N.; Sebti, S.; Engels, J. W.; Lazrek, H. B. Building blocks for polyamide nucleic acids: Facile synthesis using potassium fluoride-doped natural phosphate as basic catalyst. Nucleos. Nucleot. Nucl. 2003, 22 (2), 109-114.