Multicomponent synthesis of 1,2,3-triazol-4-yl-methylthio-3-arylquinazolin- 4(3 H)-one derivatives

Synthetic Communications

Volumn 42, Issue 16, 2012, Pages 2415-2422

  Koohshari, Majid ^a   Dabiri, Minoo ^a   Salehi, Peyman ^a   Bahramnejad, Mahboobeh ^a  

^a SHAHID BEHESHTI UNIVERSITY   (Iran)

Author keywords

1,2,3 triazole; Azide; click chemistry; propargyl bromide; quinazolinone

Indexed keywords

ALKYNE DERIVATIVE; AZIDE; QUINAZOLINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CYCLOADDITION; ONE POT SYNTHESIS;

EID: 84861507918     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397911.2011.558968     Document Type: Article

References (33)

1. Undheim, K.; Benneche, T. In Comprehensive Heterocyclic Chemistry II; Oxford: Pergamon, 1998; 6;
2. Verhaeghe, P.; Azas, N.; Gasquet, M.; Hutter, S.; Ducros, C.; Laget, M.; Rault, S.; Rathelota, P.; Vanellea, P. Bioorg. Synthesis and antiplasmodial activity of new 4-aryl-2-trichloromethylquinazolines. Med. Chem. Lett. 2008, 18, 396-401;
3. Xu, G. F.; Song, B. A.; Bhadury, P. S.; Yang, S.; Zhang, P. Q.; Jin, L. H.; Xue, W.; Hu, D. Y.; Lu, P. Synthesis and antifungal activity of novel s-substituted 6-fluoro-4-alkyl(aryl)thioquinazoline derivatives. Bioorg. Med. Chem. 2007, 15, 3768-3774. (Pubitemid 46635140)
4. Sirisoma, N.; Kasibhatla, S.; Pervin, A.; Zhang, H.; Jiang, S.; Willardsen, J. A.; Anderson, M. B.; Baichwal, V.; Mather, G. G.; Jessing, K.; Hussain, R.; Hoang, K.; Pleiman, C. M.; Tseng, B.; Drewe, J.; Cai, S. X. Discovery of 2-chloro-N-(4-methoxyphenyl)-N-methylquinazolin-4-amine (EP128265, MPI-0441138) as a potent inducer of apoptosis with high in vivo activity. J. Med. Chem. 2008, 51, 4771-4779;
5. Foote, K. M.; Mortlock, A. A.; Heron, N. M.; Jung, F. H.; Hill, G. B.; Pasquet, G.; Brady, M. C.; Green, S.; Heaton, S. P.; Kearney, S.; Keen, N. J.; Odedra, R.; Wedgea, S. R.; Wilkinsona, R. W. Synthesis and SAR of 1-acetanilide-4-aminopyrazole-substituted quinazolines: Selective inhibitors of Aurora B kinase with potent antitumor activity. Bioorg. Med. Chem. Lett. 2008, 18, 1904-1909. (Pubitemid 351391845)
6. Fowler, K. W.; Huang, D.; Kesicki, E. A.; Ooi, H. C.; Oliver, A. R.; Ruan, F.; Treiberg, J. (Icos Corporation, USA). Patents WO2005113556, 2005; US16778, 2005; Chem. Abstr. 2006, 144, 22759
7. Jiang, J. B.; Hesson, D. P.; Dusak, B. A.; Dexter, D. L.; Kang, G. J.; Hamel, E. Synthesis and biological evaluation of 2-styrylquinazolin-4(3H)-ones, a new class of antimitotic anticancer agents which inhibit tubulin polymerization. J. Med. Chem. 1990, 33, 1721-1728. (Pubitemid 20180634)
8. Takaya, Y.; Tasaka, H.; Chiba, T.; Uwai, K.; Tanitsu, M.-A.; Kim, H.-S.; Wataya, Y.; Miura, M.; Takeshita, M.; Oshima, Y. New type of febrifugine analogues, bearing a quinolizidine moiety, show potent antimalarial activity against Plasmodium malaria parasite. J. Med. Chem. 1999, 42, 3163-3166. (Pubitemid 29384052)
9. Takeuchi, Y.; Koike, M.; Azuma, K.; Nishioka, H.; Abe, H.; Kim, H.-S.; Wataya, Y.; Harayama, T. Synthesis and antimalarial activity of febrifugine derivatives. Chem. Pharm. 2001, 49, 721-725. (Pubitemid 32587119)
10. Rudolph, J.; Esler, W. P.; O'Connor, S.; Coish, P. D. G.; Wickens, P. L.; Brands, M.; Bierer, D. E.; Bloomquist, B. T.; Bondar, G.; Chen, L.; Chuang, C. Y.; Claus, T. H.; Fathi, Z.; Fu, W.; Khire, U. R.; Kristie, J. A.; Liu, X. G.; Lowe, D. B.; McClure, A. C.; Michels, M.; Ortiz, A. A.; Ramsden, P. D.; Schoenleber, R. W.; Shelekhin, T. E.; Vakalopoulos, A.; Tang, W.; Wang, L.; Yi, L.; Gardell, S. J.; Livingston, J. N.; Sweet, L. J.; Bullock, W. H. Quinazolinone derivatives as orally available ghrelin receptor antagonists for the treatment of diabetes and obesity. J. Med. Chem. 2007, 50, 5202-5216. (Pubitemid 47585718)
11. Witt, A.; Bergman, J. Recent developments in the field of quinazoline chemistry. Curr. Org. Chem. 2003, 7, 659-677. (Pubitemid 36469218)
12. Michael, J. P. Quinoline, quinazoline, and acridone alkaloids. Nat. Prod. Rep. 2002, 19, 742-760;
13. Johne, S. In Rodd's Chemistry of Carbon Compounds; M. Sainsbury, (Ed.); Elsevier: Amsterdam, 2000; Vol. 4, pp. 203-231.
14. Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Click chemistry: diverse chemical function from a few good reactions. Angew. Chem. Int. Ed. 2001, 40, 2005-2021. (Pubitemid 33644307)
15. Moses, J. E.; Moorhouse, A. D. The growing applications of click chemistry. Chem. Soc. Rev. 2007, 36, 1249-1262.
16. Tornøe, C. W.; Christensen, C.; Meldal, M. Peptidotriazoles on solid phase: [1,2,3]-Triazoles by regiospecific copper (i)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides. J. Org. Chem. 2002, 67, 3057-3064; (Pubitemid 34457265)
17. Rostovtsev V. V., Green, L. G., Fokin, V. V., Sharpless, K. B. A stepwise Huisgen cycloaddition process: Copper(i)-catalyzed regioselective "ligation" of azides and terminal alkynes. Angew. Chem., Int. Ed. 2002,41, 2596-2599; (Pubitemid 34803480)
18. Kolb, H. C., Sharpless, K. B. The growing impact of click chemistry on drug discovery. Drug Discov. Today 2004, 8, 1128-1137.
19. Wamhoff, H. In Comprehensive Heterocyclic Chemistry; A. R. Katritzky and C. W. Rees; (Eds.); Pergamon: Oxford, 1984; vol. 5, p 669;
20. Im, C.; Maiti, S. N.; Micetich, R. G.; Daneshtalab, M.; Atchison, K.; Phillips, O. A. Synthesis and b-lactamase inhibitory activity of 6-[(1-heteroarylthioethyl-1,2,3-triazol-4-yl)methylene]-penam sulfones. J. Antibiot. 1994, 47, 1030-1040. (Pubitemid 24309837)
21. Gouault, N.; Cupif, J.-F.; Sauleau, A.; David, M. c-Methyl-substituted-c- butyrolactones: Solid-phase synthesis employing a cyclisation-cleavage strategy. Tetrahedron Lett. 2000, 41, 7293-7297.
22. Moorhouse, A. D.; Moses, J. E. Microwave enhancement of a "one-pot" tandem azidation-"click" cycloaddition of anilines. Synlett 2008, 2089-2092.
23. Gonda, Z.; Novák, Z. Highly active coppercatalysts for azide-alkyne cycloaddition. Dalton Trans. 2010, 39, 726-729.
24. Grieco, P. A.; (Ed.). Organic Synthesis in Water; Blackie: London, 1998;
25. Li, C.-J.; Chen, L. Organic chemistry in water. Chem. Soc. Rev. 2006, 35, 68-82. (Pubitemid 43485014)
26. Dallinger, D.; Kappe, C. O. Microwave-assisted synthesis in water as solvent. Chem. Rev. 2007, 107, 2563-2591. (Pubitemid 47029100)
27. Liotta, C. L.; Hallett, J. P.; Pollet, P.; Eckert, C. A. In Organic Reactions in Water: Principles, Strategies and Applications; U. M., Lindstrom (Ed.); Blackwell: Oxford, UK, 2007; pp. 256-300.
28. Nakamura, K.; Matsuda, T. In Organic Reactions in Water: Principles, Strategies, and Applications; Lindstrom, U. M., (Ed.); Blackwell: Oxford, UK, 2007; pp. 301-349.
29. Dabiri, M.; Salehi, P.; Bahramnejad, M.; Sherafat, F. Synthesis of diheterocyclic compounds based on triazolyl methoxy phenylquinazolines via a one-pot, four-component-click reaction. J. Comb. Chem. 2010, 12, 638-642;
30. Baghbanzadeh, M.; Molnar, M.; Damm, M.; Reidlinger, C.; Dabiri, M.; Kappe, C. O. Parallel microwave synthesis of 2-styrylquinazolin-4(3H)-ones in a high-throughput platform using HPLC=GC vials as reaction vessels. J. Comb. Chem. 2009, 11, 676-684;
31. Salehi, P.; Dabiri, M.; Baghbanzadeh, M.; Bahramnejad, M. One-pot, three-component synthesis of 2,3-dihydro-4(1H)-quinazolinones by montmorillonite K-10 as an efficient and reusable catalyst. Synth. Commun. 2006, 16, 2287-2292. (Pubitemid 44266679)
32. Ghiviriga, I.; El-Gendy, B. E.-D. M.; Steel, P. J.; Katritzky, A. R. Tautomerism of guanidines studied by 15N NMR: 2-Hydrazono-3-phenylquinazolin- 4(3H)-ones and related compounds. Org. Biomol. Chem. 2009, 7, 4110-4119.
33. Bräse, S.; Banert, K. Organic Azides Syntheses and Applications Part 1; John Wiley & Sons Ltd.: Chichester, UK, 2010; 1-28.