The synthesis of highly fluorescent heterocyclic compounds: Pyrido[2',1':2,3]imidazo[4,5-b]quinoline-12-yl cyanides

Dyes and Pigments

Volumn 86, Issue 3, 2010, Pages 266-270

  Rahimizadeh, Mohammad ^a   Pordel, Mehdi ^a   Bakavoli, Mehdi ^a   Eshghi, Hossein ^a  

^a FERDOWSI UNIVERSITY OF MASHHAD   (Iran)

Author keywords

Absorption; Dye; Emission; Fluorescence; Imidazo 1,2 a pyridine; Quinolines

Indexed keywords

ABSORPTION DYE; FLUORESCENCE PROPERTIES; HETEROCYCLIC COMPOUND; HETEROCYCLIZATIONS; HYDROXYL GROUPS; NUCLEOPHILIC SUBSTITUTIONS;

ABSORPTION; CYANIDES; PYRIDINE; SYNTHESIS (CHEMICAL);

FLUORESCENCE;

ABSORPTION; FLUORESCENCE; ORGANIC DYE; SYNTHESIS;

EID: 77950864256     PISSN: 01437208     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.dyepig.2010.01.013     Document Type: Article

References (28)

1. Hunger K. Industrial dyes. Weinheim, Germany: WILEY-VCH Verlag, Gmbh and Co. KGaA 2003; p.569-572.
2. Dmitry A., Pavel A. Dipyrrolyl quinoxalines with extended chromophores are efficient fluorimetric sensors for pyrophosphate. Chemical Communication 2003, 12:1394-1395.
3. Gold H. In the chemistry of synthetic dyes. Pergamon 1971, 535-542. Academic Press, New York, USA. H. Venkataraman (Ed.).
4. Belgodere E., Bossio R., Chimichi S., Passini V., Pepino R. Synthesis and fluorescence of some thiazole and benzothiazole derivatives. Dyes and Pigments 1985, 4(1):59-71.
5. Kalle A.G. British Patent 1962, 895(001).
6. Ramasamy S.M., Hurtubise R.J. Effects of temperature on the solid-surface luminescence properties of benzo[f]quinoline adsorbed on filter paper. Applied Spectroscopy 1989, 43(4):616-621.
7. Nolan E.M., Jaworski J., Okamoto K.I., Hayashi Y., Sheng M., Lippard S.J. QZ1 and QZ2: rapid, reversible quinoline-derivatized fluoresceins for sensing biological Zn (II). Journal of the American Chemical Society 2005, 127(48):16812-16823.
8. Hranjec M., Kralj M., Piantanida I., Sedić M., Šuman L., Pavelić K., et al. Novel cyano- and amidino-substituted derivatives of styryl-2-benzimidazoles and benzimidazo[1,2-a]quinolines. Synthesis, photochemical synthesis, DNA binding, and antitumor evaluation, part 3. Journal of Medicinal Chemistry 2007, 50(23):5696-5711.
9. Zhang N., Zhao Y.-Z., Zhang H.-S., Wang H. Sensitive determination of aliphatic amines by high-performance liquid chromatography with a new fluorogenic probe 3-(4-fluorinebenzoyl)-2-quinoline carboxaldehyde. Journal of Separation Science 2008, 31(1):38-46.
10. Shiraishi Y., Ichimura C., Hirai T. A quinoline-polyamine conjugate as a fluorescent chemosensor for quantitative detection of Zn(II) in water. Tetrahedron Letters 2007, 48(44):7769-7773.
11. 2+ ion in natural water. Chemical Communications 2006, 42:4392-4394.
12. Musiol R., Tabak D., Niedbala H., Podeszwa B., Jampilek J., Kralova K., et al. Investigating biological activity spectrum for novel quinoline analogues 2: hydroxyquinolinecarboxamides with photosynthesis-inhibiting activity. Bioorganic and Medicinal Chemistry 2008, 16(8):4490-4499.
13. Tseng C.-H., Chen Y.-L., Lu P.-J., Yang C.-N., Tzeng C.-C. Synthesis and antiproliferative evaluation of certain indeno[1,2-c]quinoline derivatives. Bioorganic and Medicinal Chemistry 2008, 16(6):3153-3162.
14. Clarke H.T., Davis A.W. Quinoline. Organic Syntheses 1922, 2:79-83.
15. Combes A. Quinoline synthesis. Bulletin de la Societe Chimique de France 1888, 49:89-94.
16. Friedländer P. Quinoline synthesis. Chemische Berichte 1882, 15:2572-2575.
17. Kobayashi K., Takanohashi A., Himei Y., Sano T., Fukamachi S., Morikawa O., et al. A new method for the synthesis of pyrrolo[1,2-a]quinolines based on boron trifluoride-mediated cyclization of 1-(2-oxiranylphenyl)pyrroles. Heterocycles 2007, 71(12):2717-2720.
18. D'yachenko E.V., Glukhareva T.V., Nikolaenko E.F., Tkachev A.V., YuYu Morzherin Synthesis of hydrogenated spiro derivatives of quinolines. Russian Chemical Bulletin 2004, 53(6):124012-124047.
19. MaĶosza M., Wojciechowski K. Nucleophilic aromatic substitution of hydrogen as a tool for the synthesis of indole and quinoline derivatives. Heterocycles 2001, 54(1):445-474.
20. Kovalska V.B., Losytskyy M.Y., Kryvorotenko D.V., Balanda A.O., Tokar V.P., Yarmoluk S.M. Synthesis of novel fluorescent styryl dyes based on the imidazo[1,2-a]pyridinium chromophore and their spectral-fluorescent properties in the presence of nucleic acids and proteins. Dyes and Pigments 2006, 68(1):39-45.
21. Laquintana V., Denora N., Lopedota A., Suzuki H., Sawada M., Serra M., et al. N-benzyl-2-(6,8-dichloro-2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)-N-(6-(7-nitrobenzo[c][1,2,5]oxadiazol-4-ylamino)hexyl)acetamide as a new fluorescent probe for peripheral benzodiazepine receptor and microglial cell visualization. Bioconjugate Chemistry 2007, 18(5):1397-1407.
22. Rahimizadeh M., Pordel M., Bakavoli M., Bakhtiarpoor Z., Orafaie A. Synthesis of imidazo[4,5-a]acridones and imidazo[4,5-a]acridines as potential antibacterial agents. Monatshefte fur Chemie 2009, 140(6):633-638.
23. Rahimizadeh M., Pordel M., Bakavoli M., Rezaeian Sh Synthesis of a new heterocyclic system - Fluoreno[1,2-d]imidazol-10-one. Canadian Journal of Chemistry 2009, 87(6):724-728.
24. Rahimizadeh M., Pordel M., Bakavoli M., Eshghi H., Shiri A. Vicarious nucleophilic substitution in nitro derivatives of imidazo[1,2-a]pyridine. Mendeleev Communications 2009, 19(3):161-162.
25. Bakavoli M., Pordel M., Rahimizadeh M., Jahandari P., Seresht E.R. Sulfuric acid mediated heterocyclization of Ortho-cyanomethylnitroarenes to benzo[C]isoxazoles and fused benzo[C]isoxazoles. Heterocycles 2008, 75(1):165-171.
26. Umberger J.Q., LaMer V.V. The kinetics of diffusion controlled molecular and ionic reactions in solution as determined by measurements of the quenching of fluorescence. Journal of the American Chemical Society 1945, 67(7):1099-1109.
27. Paolini J.P., Robins R.K. Substitution reactions of imidazo[1,2-a]pyridine and related methyl derivatives. Journal of Organic Chemistry 1965, 30(12):4085-4090.
28. Davis R.B., Pizzini L.C. Condensation of aromatic nitro compounds with acrylacetonitriles. Journal of Organic Chemistry 1960, 25(11):1884-1888.