A microwave-assisted and heteropolyacids-catalysed cyclocondensation reaction for the synthesis of 4(3H)-quinazolinones

Molecules

Volumn 13, Issue 4, 2008, Pages 779-789

  Ighilahriz, Karima ^a   Boutemeur, Baya ^a   Chami, Fariza ^a   Rabia, Cherifa ^a   Hamdi, Maâmar ^a   Hamdi, Safouane M ^b  

^a UNIVERSITY OF SCIENCES AND TECHNOLOGY HOUARI BOUMEDIENE   (Algeria)

^b TOULOUSE UNIVERSITY HOSPITAL   (France)

Author keywords

4(3H) Quinazolinones; Heteropolyacids; Microwave irradiation; Solvent free synthesis

Indexed keywords

ACID; ANILINE; ANILINE DERIVATIVE; ANTHRANILIC ACID; ANTHRANILIC ACID DERIVATIVE; QUINAZOLINONE DERIVATIVE; SOLVENT;

ARTICLE; CATALYSIS; CHEMISTRY; MICROWAVE RADIATION; SYNTHESIS;

ACIDS; ANILINE COMPOUNDS; ANTHRANILIC ACIDS; CATALYSIS; MICROWAVES; QUINAZOLINONES; SOLVENTS;

EID: 43049086303     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules13040779     Document Type: Article

References (27)

1. Pereira, M. F.; Chevrot, R.; Rosenfeld, E.; Thiery, V.; Besson, T. Synthesis and evaluation of the antimicrobial activity of novel quinazolinones. J. Enzym. Inhib. Med. Chem. 2007, 22, 577-583.
2. Kacker, I. K.; Zaheer, S. H. Potential analgesics.1. Synthesis of substituted 4-quinazolinones. J. Indian Chem. Soc. 1951, 28, 344-346.
3. Brumas, B. V.; Fiallo, M. M. L.; Berthon, G. Copper(II) interactions with non-steroidal antiinflammatory reagents. J. Inorg. Biochem. 2006, 100, 362-373.
4. Tamaoki, S.; Yamauchi, Y.; Nakano, Y.; Sakano, S.; Asagarasu, A.; Sato, M. Pharmacological properties of 3-amino-5,6,7,8-tetrahydro-2-{4-[4-(quinolin-2- yl) piperazin-1-yl]butyl}quinazolin-4(3H)-one (TZB-30878), a novel therapeutic agent for diarrhea-predominant irritable bowel syndrome (IBS) and its effects on an experimental IBS model. J. Pharm. Exp. Ther. 2007, 322, 1315-1323.
5. Welch, W. M.; Ewing, F. E.; Huang J.; Menniti, F.S.; Pagnozzi, M. J.; Kelly, K.; Seymour, P. A.; Guanowsky, V.; Guhan, S.; Guinn, M. R.; Critchett, D.; Lazzro, J.; Ganong, A. H. ; DeVries, K. M.; Staigers, T. L.; Chenard, B. L. Atropisomeric quinazolin-4-one derivatives are potent noncompetitive α-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid (AMPA) receptor antagonists. Bioorg. Med. Chem. Lett. 2001, 11, 177-181.
6. Saleh, M.; Hafez, Y.; Abdel-Hay, F.; Gad, G. Synthesis and biological activities of some new 3H-quinazolin-4-one derivatives derived from 3-phenylamino-2-thioxo-3H-quinazolin-4-one. Phosphorus, Sulfur Silicon Relat. Elem. 2004, 179, 411-426.
7. Errede, L. A.; MeBrady, J. J.; Oien, H. T. Acylanthranils. 4 The effect of steric hindrance on selectivity in the reaction of amines with acetylanthranil. J. Org. Chem. 1977, 42, 656-658.
8. Witt, A.; Bergman, J. Synthesis of reactions of some 2-vinyl-3H-quinazolin-4-ones. Tetrahedron 2000, 56, 7248-7253.
9. Kidwai, M.; Rastogi, S.; Mohan, R. A novel route to the Niementowsky reaction. Croat. Chem. Acta 2003, 76, 365-369.
10. Liu, J. F.; Lee, J.; Dalton, M. A.; Bi, G.; Yu, L.; Baldino, C. M.; McElory, E.; Brown, M. Microwave-assisted one-pot synthesis of 2,3-disubstituted 3H-quinazolin-4-ones. Tetrahedron Lett. 2005, 46, 1241-1244.
11. Dandia, A.; Singh, R.; Sarawgi, P. Green chemical multi-component one-pot synthesis of fluorinated 2,3-disubstituted quinazolin-4(3H)-ones under solvent free conditions and their antifungal activity. J. Fluor. Chem. 2005, 126, 307-312.
12. Rad- Moghadam, K and S. Khajavi, M. One pot synthesis of substituted Quinazolin-4(3H)-ones under microwave irradiation. J. Chem. Res. (S) 2006, 702-703.
13. Rad-Moghadam, K.; Mohseni M. An expeditious and solvent-free route to the synthesis of 2-substituted quinazolin-4(3H)-ones under microwave conditions. J. Chem. Res. 2003, 487-488.
14. Connolly, D.J.; Cusack, D.; O'Sullivan, T.P.; Guiry, P.J. Synthesis of quinazolinones and quinazolines. Tetrahedron 2005, 61, 10152-10202.
15. Kostakis, I.K.; Elomri, A.; Seguin, E.; Iannelli, M.; Besson, T. Rapid synthesis of 2,3-disubstituted-quinazolin-4-ones enhanced by microwave-assisted decomposition of formamide. Tetrahedron Lett. 2007, 48, 6609-6613.
16. 3- catalyzed one-pot synthesis of quinazolin-4(3H)-ones from anthranilic acid, amines and orthoesters (or formic acid) in solvent-free conditions. Synthesis 2003, 1241-1247.
17. 3: An efficient and recyclable heterogenous catalyst for one step synthesis of 4(3H)-quinazolinones under solvent free conditions. Catal. Commun. 2006, 7, 787-790.
18. 4: a new, efficient and reusable promoter system for the synthesis of 4(3H)-quinazolinone derivatives. Tetrahedron Lett. 2006, 47, 3561-3564.
19. Lingaiah, V. B.; Ezikiel, G. T. Yakaiah; Reddy, V. G.; Rao, P. S. Nafion-H: An Efficient and Recyclable Heterogeneous Catalyst for the One-Pot Synthesis of 2,3-Disubstituted 4(3H)-Quinazolinones under Solvent-Free Microwave Irradiation Conditions. Synlett 2006, 2507-2509.
20. Narasimhulu, M.; Mahesh, K. C.; Reddy, T. S.; Rajesh, K.; Venkateswarlu, Y. Lanthanum (III) nitrate hexahydrate or p-toluenesulfonic acid catalyzed one-pot synthesis of 4(3H)-quinazolinones under solvent-free conditions. Tetrahedron Lett. 2006, 47, 4381-4383.
21. Kozhevnikov, I.V. Catalysts for Fine Chemical Synthesis, Vol. 2, Catalysis by Polyoxometalates. Wiley: New York. 2002; pp. 61-109.
22. Timofeeva, M. N. Acid catalysis by heteropoly acids. Appl. Catal. A 2003, 256, 19-35.
23. Rafiee, E.; Jafari, H. A pratical and green approach towards synthesis of dihydropyrimidinones: using hetropolyacids as efficient catalysts. Bioorg. Med. Chem. Lett. 2006, 16, 2463-2466.
24. 40. J. Mol. Catal. A-Chem. 2006, 249, 1-3.
25. Hedidi, M.; Hamdi, S. M.; Mazari, T.; Boutemeur, B.; Rabia, C.; Chemat, F.; Hamdi, M. Microwave-assisted synthesis of calix[4]resorcinarenes. Tetrahedron 2006, 62, 5652-5655.
26. Pope, M. T. Heteropoly and Isopolyoxometallates. Springer: Berlin. 1983.
27. Nüchter, M.; Ondruschka, B.; Bonrath, W.; Gum, A. Microwave assisted synthesis-a critical technology overview. Green Chem. 2004, 6, 128-141.