A green multicomponent synthesis of bioactive pyrimido[4,5-b]quinoline derivatives as antibacterial agents in water catalyzed by RuCl 3·xH2O

Chinese Chemical Letters

Volumn 25, Issue 2, 2014, Pages 308-312

  Tabatabaeian, Khalil ^a   Shojaei, Abdollah Fallah ^a   Shirini, Farhad ^a   Hejazi, Seyyedeh Zoha ^a   Rassa, Mehdi ^a  

^a UNIVERSITY OF GUILAN   (Iran)

Author keywords

Antibacterial activity; One pot multicomponent reaction; Pyrimido 4,5 b quinoline; Reusable homogenous catalyst; Water

Indexed keywords

EID: 84895909302     PISSN: 10018417     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cclet.2013.10.021     Document Type: Article

References (33)

1. P.A. Grieco Organic Synthesis in Water 1998 Thomson Science London 1 278
2. R. Breslow, and U. Maitra On the origin of product selectivity in aqueous Diels-Alder reactions Tetrahedron Lett. 25 1984 1239 1240
3. D.C. Rideout, and R. Breslow Hydrophobic acceleration of Diels-Alder reactions J. Am. Chem. Soc. 102 1980 7816 7817
4. S. Narayan, J. Muldoon, and M.G. Finn et al. On water: unique reactivity of organic compounds in aqueous suspension Angew. Chem. Int. Ed. 44 2005 3275 3279
5. B. Sharifzadeh, N.O. Mahmoodi, and M. Mamaghani et al. Facile regioselective synthesis of novel bioactive thiazolyl-pyrazolinederivatives via a three-component reaction and their antimicrobial activity Bioorg. Med. Chem. Lett. 23 2013 548 551
6. R. Hossein nia, M. Mamaghani, K. Tabatabaeian, F. Shirini, and M. Rassa An expeditious regioselective synthesis of novel bioactive indole-substituted chromene derivatives via one-pot three-component reaction Bioorg. Med. Chem. Lett. 22 2012 5956 5960
7. C.C.A. Cariou, G.J. Clarkson, and M.J. Shipman Rapid synthesis of 1,3,4,4′-tetrasubstituted βlactams from methyleneaziridines using a 4-component reaction Org. Chem. 73 2008 9762 9764
8. B.M. Trost Atom economy. A challenge for organic synthesis, homogeneous catalysis leads the way Angew. Chem. Int. Ed. Engl. 34 1995 259 281
9. L.F. Tietze Domino reactions in organic synthesis Chem. Rev. 96 1996 115 136
10. H. Waldmann Domino reaction Organic Synthesis Highlight II 1995 VCH Weinheim 193 202
11. A.M. Triggle, E. Shefter, and D.J. Triggle Crystal structures of calcium channel antagonists: 2,6-dimethyl-3,5-dicarbomethoxy-4-[2-nitro-3-cyano-4- (dimethylamino)-, and 2,3,4,5,6-pentafluorophenyl]-1,4-dihydropyridine J. Med. Chem. 23 1980 1442 1445
12. R. Fossheim, K. Svarteng, and A. Mostad et al. Crystal structures and pharmacological activity of calcium channel antagonists: 2,6-dimethyl-3,5- dicarbomethoxy-4-(unsubstituted, 2-methyl-, 4-methyl-, 3-nitro-, 4-nitro-, and 2,4-dinitrophenyl)-1,4-dihydropyridine J. Med. Chem. 25 1982 126 131
13. R.P. Mason, I.T. Mark, M.W. Trumbore, and P.E. Masson Antioxidant properties of calcium antagonists related to membrane biophysical interactions Am. J. Cardiol. 84 1999 16 22
14. G.K. Verma, K. Raghuvanshi, R. Kumar, and M.S. Singh An efficient one-pot three-component synthesis of functionalized pyrimido[4,5-b]quinolines and indeno fused pyrido[2,3-d]pyrimidines in water Tetrahedron Lett. 53 2012 399 402
15. D.Q. Shi, S.N. Ni, and F. Yang et al. An efficient synthesis of pyrimido[4,5-b]quinoline and indeno[2′,1′:5,6]pyrido[2,3-d] pyrimidine derivatives via multicomponent reactions in ionic liquid J. Heterocycl. Chem. 45 2008 693 702
16. N.A. Hassan, M.I. Hegab, and A.I. Hashem et al. Three-component, one-pot synthesis of pyrimido[4,5-b]-quinoline and pyrido[2,3-d]pyrimidine derivatives J. Heterocycl. Chem. 44 2007 775 782
17. 4 encapsulated-silica particles bearing sulfonic acid groups as a magnetically separable catalyst for green and efficient synthesis of functionalized pyrimido[4,5-b]quinolines and indeno fused pyrido[2,3-d]pyrimidines in water Chin. Chem. Lett. 24 2013 370 372
18. H.Y. Guo, and Y. Yu One-pot synthesis of 7-aryl-11,12-dihydrobenzo[h] pyrimido-[4,5-b]quinoline-8,10(7H,9H)-diones via three-component reaction in ionic liquid Chin. Chem. Lett. 21 2010 1435 1438
19. Y.S. Sanghhvi, S.B. Larson, and S.S. Matsumoto et al. Antitumor and antiviral activity of synthetic alpha- and beta-ribonucleosides of certain substituted pyrimido[5,4-d]pyrimidines: a new synthetic strategy for exocyclic aminonucleosides J. Med. Chem. 32 1989 629 637
20. R.B. Tenser, A. Gaydos, and K.A. Hay Inhibition of herpes simplex virus reactivation by dipyridamole Antimicrob. Agents Chemother. 45 2001 3657 3659
21. J.P. De la Cruz, T. Carrasco, G. Ortega, and F. Sanchez De la Cuesta Inhibition of ferrous-induced lipid peroxidation by pyrimido-pyrimidine derivatives in human liver membranes Lipid 27 1992 192 194
22. B.S. Holla, M. Mahalinga, M.S. Karthikeyan, P.M. Akberali, and N.S. Shetty Synthesis of some novel pyrazolo[3,4-d]pyrimidine derivatives as potential antimicrobial agents Bioorg. Med. Chem. 14 2006 2040 2047
23. H.C. Aspinall Chiral lanthanide complexes: coordination chemistry and applications Chem. Rev. 102 2002 1807 1850
24. H. Yu, M.S. Zhang, and L.R. Cui Copper-catalyzed synthesis of 1,2-disubstituted benzimidazoles from imidoyl chlorides Chin. Chem. Lett. 23 2012 573 575
25. I. Murahashi Ruthenium in Organic Synthesis 2004 Wiley-VCH New York
26. III-catalyzed condensation of indoles and aldehydes or ketones Can. J. Chem. 84 2006 1541 1545
27. K. Tabatabaeian, M. Mamaghani, N.O. Mahmoodi, and A. Khorshidi Ultrasonic-assisted ruthenium-catalyzed oxidation of aromatic and heteroaromatic compounds Catal. Commun. 9 2008 416 420
28. III-catalyzed double-conjugate 1,4-addition of indoles to symmetric enones J. Mol. Catal. A: Chem. 270 2007 112 116
29. K. Tabatabaeian, M. Mamaghani, N.O. Mahmoodi, and A. Khorshidi Solvent-free, ruthenium-catalyzed, regioselective ring-opening of epoxides, an efficient route to various 3-alkylated indoles Tetrahedron Lett. 49 2008 1450 1454
30. K. Tabatabaeian, M. Mamaghani, N.O. Mahmoodi, and A. Khorshidi Ruthenium-catalyzed efficient routes to oxindole derivatives Can. J. Chem. 87 2009 1213 1217
31. K. Tabatabaeian, M. Mamaghani, N.O. Mahmoodi, and A. Khorshidi Diastereoselective ruthenium-catalyzed Michael addition of indoles to hormone steroids: an efficient route to new indole derivatives Synth. Commun. 40 2010 1677 1684
32. K. Tabatabaeian, A. Khorshidi, M. Mamaghani, A. Dadashi, and M. Khoshnood Jalali One-pot synthesis of tetrahydrobenzo[a]xanthen-11-one derivatives catalyzed by ruthenium chloride hydrate as a homogeneous catalyst Can. J. Chem. 89 2011 623 627
33. A. Khorshidi Indole cyanation via CH bond activation under catalysis of Ru(III)-exchanged NaY zeolite (RuY) as a recyclable catalyst Chin. Chem. Lett. 23 2012 903 906