Pentafluorophenylammonium triflate (PFPAT) catalyzed facile construction of substituted chromeno[2,3-d]pyrimidinone derivatives and their antimicrobial activity

Journal of Advanced Research

Volumn 5, Issue 2, 2014, Pages 209-218

  Ghashang, Majid ^a   Mansoor, Syed Sheik ^b   Aswin, Krishnamoorthy ^b  

^a ISLAMIC AZAD UNIVERSITY   (Iran)

^b C ABDUL HAKEEM COLLEGE   (India)

Author keywords

2 Amino 3 cyano 6 methyl 4 phenyl 4H pyran 5 ethylcarboxylate; Antimicrobial activity; Chromeno 2,3 d pyrimidinones; Coumarin 3 carboxylic acid; Pentafluorophenylammonium triflate

Indexed keywords

EID: 84897609130     PISSN: 20901232     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jare.2013.03.003     Document Type: Article

References (34)

1. Curir P., Galeotti F., Marcello D., Barile E., Lanzotti V. Pavietin, a coumarin from Aesculus pavia with antifungal activity. J Nat Prod 2007, 70(10):1668-1671.
2. Al-Amiery A.A., Al-Bayati R.I.H., Saour K.Y., Radi M.F. Cytotoxicity, antioxidant and antimicrobial activities of novel 2-quinolone derivatives derived from coumarin. Res Chem Intermed 2012, 38:559-569.
3. Zhan W.-H., Hua J.-L., Jin Y.-H., Teng X., Tian H. The synthesis and characterization of novel coumarin-containing cyanine dyes via "Click" chemistry. Res Chem Intermed 2008, 34:229-239.
4. Sashidhara K.V., Kumar A., Kumar M., Sarkar J., Sinha S. Synthesis and in vitro evaluation of novel coumarin-chalcone hybrids as potential anticancer agents. Bioorg Med Chem Lett 2010, 20:7205-7211.
5. Gursoy A., Karali N. Synthesis, characterization and primary antituberculosis activity evaluation of 4-(3-coumarinyl)-3-benzyl-4-thiazolin-2-one benzylidenehydrazones. Turk J Chem 2003, 27:545-551.
6. Ma T., Liu L., Xue H., Li L., Han C., Wang L., et al. Chemical library and structure-activity relationships of 11-demethyl-12-oxo calanolide A analogues as anti-HIV-1 agents. J Med Chem 2008, 51(5):1432-1446.
7. Kontogiorgis C.A., Hadjipavlou L.D. Synthesis and biological evaluation of novel coumarin derivatives with a 7-azomethine linkage. Bioorg Med Chem Lett 2004, 14:611-614.
8. Sashidhara K.V., Rosaiah J.N., Kumar A., Bhatia G., Khanna A.K. Synthesis of novel benzocoumarin derivatives as lipid lowering agents. Bioorg Med Chem Lett 2010, 20:3065-3069.
9. Bansala Y., Ratraa S., Bansala G., Singhb I., Aboul-Eneinc H.Y. Design and synthesis of coumarin substituted oxathiadiazolone derivatives having anti-inflammatory activity possibly through p38 MAP kinase inhibition. J Iran Chem Soc 2009, 6(3):504-509.
10. Olayinka O.A., Obinn C.N. Microwave-assisted synthesis and evaluation of antimicrobial activity of 3-(3-(s-aryl and s-heteroaromatic)acryloyl)-2H-chromen-2-one derivatives. J Heterocycl Chem 2010, 47:179-187.
11. Ghosh P.P., Das A.R. Nano crystalline ZnO: a competent and reusable catalyst for one pot synthesis of novel benzylamino coumarin derivatives in aqueous media. Tetrahedron Lett 2012, 53:3140-3143.
12. Khoobi M., Ramazani A., Foroumadi A.R., Hamadi H., Hojjati Z., Shafiee A. Efficient microwave-assisted synthesis of 3-benzothiazolo and 3-benzothiazolino coumarin derivatives catalyzed by heteropoly acids. J Iran Chem Soc 2011, 8(4):1036-1042.
13. Khurana J.M., Kumar S. Tetrabutylammonium bromide (TBAB): a neutral and efficient catalyst for the synthesis of biscoumarin and 3,4-dihydropyrano[c]chromene derivatives in water and solvent-free conditions. Tetrahedron Lett 2009, 50:4125-4127.
14. Banothu J., Bavanthula R. Brønsted acidic ionic liquid catalyzed highly efficient synthesis of chromeno pyrimidinone derivatives and their antimicrobial activity. Chin Chem Lett 2012, 23:1015-1018.
15. Zhou J.-F., Gong G.-X., An L.-T., Liu Y., Zhu F.-X., Zhu Y.-L. An efficient synthesis of quinoxalines under catalyst-free and microwave-irradiation conditions. Synlett 2008, 20:3163-3166.
16. Funatomi T., Wakasugi K., Misaki T., Tanabe Y. Pentafluorophenylammonium triflate (PFPAT): an efficient, practical, and cost-effective catalyst for esterification, thio esterification, trans esterification, and macrolactone formation. Green Chem 2006, 8:1022-1027.
17. Iida A., Osada J., Nagase R., Misaki T., Tanabe Y. Mild and efficient pentafluoro phenylammonium triflate (PFPAT)-catalyzed C-acylations of enol silyl ethers or ketene silyl (thio)acetals with acid chlorides. Org Lett 2007, 9:1859-1862.
18. Nagase R., Osada J., Tamagaki H., Tanabe Y. Pentafluorophenylammonium trifluoromethanesulfonamide: mild, powerful, and robust catalyst for Mukaiyama aldol and Mannich reactions between ketene silyl acetals and ketones or oxime ethers. Adv Synth Catal 2010, 352:1128-1134.
19. Khaksar S., Zakeri H. Pentafluorophenylammonium triflate as a mild and new organocatalyst for acylation of alcohols, phenols, and amines under solvent-free condition. Comb Chem High Throughput Screen 2012, 15(7):576-579.
20. Khaksar S., Behzadi N. Pentafluorophenylammonium triflate (PFPAT): an efficient, practical, and cost-effective catalyst for one-pot condensation of β-naphthol, aldehydes and cyclic 1,3-dicarbonyl compounds. Comb Chem High Throughput Screen 2012, 15(10):845-848.
21. Khaksar S., Behzadi N. Mild and highly efficient method for synthesis of 14-aryl(alkyl)-14H-dibenzo[a, j]xanthenes and 1,8-dioxooctahydroxanthene derivatives using pentafluorophenyl ammonium triflate as a novel organocatalyst. Chin J Catal 2012, 33(6):982-985.
22. Khaksar S., Vahdat S.M., Moghaddamnejad R.N. Pentafluorophenylammonium triflate: an efficient, practical, and cost-effective organocatalyst for the Biginelli reaction. Monatsh Chem 2012, 143:1671-1674.
23. Mansoor S.S., Aswin K., Logaiya K., Sudhan S.P.N. [Bmim]BF4 ionic liquid: an efficient reaction medium for the one-pot multi-component synthesis of 2-amino-4,6 diphenyl pyridine-3-carbonitrile derivatives. J Saudi Chem Soc 2012, http://dx.doi.org/10.1016/j.jscs.2012.07.011.
24. Mansoor S.S., Aswin K., Logaiya K., Sudhan S.P.N. An efficient one-pot multi component synthesis of polyhydroquinoline derivatives through Hantzsch reaction catalysed by gadolinium triflate. Arab J Chem 2012, http://dx.doi.org/10.1016/j.arabjc.2012.10.017.
25. 2) under solvent-free conditions. Res Chem Intermed 2014, 40:1135-1145.
26. Ghashang M. Bismuth nitrate as an efficient catalyst for the preparation of 2-arylbenzothiazole derivatives. Res Chem Intermed 2013, doi:10.1007/s11164-013-1072-9.
27. Pratap U.R., Jawale D.V., Netankar P.D., Mane R.A. Baker's yeast catalyzed one-pot three-component synthesis of polyfunctionalized 4H-pyrans. Tetrahedron Lett 2011, 52:5817-5819.
28. Kumar D., Reddy V.B., Sharad S., Dube U., Kapur S. A facile one-pot green synthesis and antibacterial activity of 2-amino-4H-pyrans and 2-amino-5-oxo-5,6,7,8-tetrahydro-4H-chromenes. Eur J Med Chem 2009, 44:3805-3809.
29. Jin T.-S., Wang A.-Q., Shi F., Han L.-S., Liu L.-B., Li T.-S. Hexadecyldimethyl benzyl ammonium bromide: an efficient catalyst for a clean one-pot synthesis of tetrahydrobenzopyran derivatives in water. ARKIVOC 2006, (xiv):78-86.
30. Nemouchi S., Boulcina R., Carboni B., Debache A. Phenylboronic acid as an efficient and convenient catalyst for a three-component synthesis of tetrahydrobenzo[b]pyrans. C R Chimie 2012, 15:394-397.
31. Khaksar S., Rouhollahpour A., Talesh S.M. A facile and efficient synthesis of 2-amino-3-cyano-4H-chromenes and tetrahydrobenzo[b]pyrans using 2,2,2-trifluoroethanol as a metal-free and reusable medium. J Fluorine Chem 2012, 141:11-15.
32. 2) as an efficient and reusable catalyst. Chem Pap 2011, 65(5):714-720.
33. Foucourt A., Dubouilh-Benard C., Chosson E., Corbière C., Buquet C., Iannelli M., Leblond B., Marsais F., Besson T. Microwave-accelerated Dimroth rearrangement for the synthesis of 4-anilino-6-nitroquinazolines. Application to an efficient synthesis of a microtubule destabilizing agent. Tetrahedron 2010, 66:4495-4502.
34. Dimroth O. Ueber intramolekulare Umlagerungen. Umlagerungen in der Reihe des 1, 2, 3-triazols. Justus Liebigs Annalen der Chemie 1909, 364:183-226.