The introduction of OH and COOH groups into 4H-imidazoles: Water-soluble functional dyes and quinomethides

Synthesis

Volumn , Issue 18, 2008, Pages 2957-2962

  Matschke, Martin ^a   Beckert, Rainer ^a   Kubicova, Lenka ^a   Biskup, Christoph ^a  

^a FRIEDRICH SCHILLER UNIVERSITY JENA   (Germany)

Author keywords

Carboxylic acids; Functional dyes; Heterocycles; Quinomethides; Tautomerism

Indexed keywords

NAPHTHALENE; OFFSHORE OIL WELL PRODUCTION; SULFUR COMPOUNDS;

CARBOXYLIC ACIDS; FUNCTIONAL DYES; HETEROCYCLES; QUINOMETHIDES; TAUTOMERISM;

PLANTS (BOTANY);

2 [5 (4 TOLYLAMINO) 4 (4 TOLYLIMINO) 4H IMIDAZOL 2 YL]BENZENESULFONIC ACID; 2 [5 (4 TOLYLAMINO) 4 (4 TOLYLIMINO) 4H IMIDAZOL 2 YL]BENZOIC CID; 2,6 DI TERT BUTYL 4 [4 (4 TOLYLAMINO) 5 (4 TOLYLIMINO) 1,5 DIHYDRO 2H IMIDAZOL 2 YLIDENE]CYCLOHEXA 2,5 DIENONE; 2,6 DI TERT BUTYL 4 [4 ,5 BIS(4 TOLYLAMINO) 1H IMIDAZOL 2 YL]PHENOL; 2,6 DI TERT BUTYL 4 [4 ,5 BIS[(4 TERT BUTYLPHENYL)AMINO] 1H IMIDAZOL 2 YL]PHENOL; 2,6 DI TERT BUTYL 4 [4 [(4 TERT BUTYLPHENYL)AMINO] 5 [(4 TERT BUTYLPHENYL)IMINO] 1,5 DIHYDRO 2H IMIDAZOL 2 YLIDENE]CYCLOHEXA 2,5 DIENONE; 2,6 DI TERT BUTYL 4 [4 [[4 (DIMETHYLAMINO)PHENYL]AMINO] 5 [[4 (DIMETHYLAMINO)PHENYL]IMINO] 1,5 DIHYDRO 2H IMIDAZOL 2 YLIDENE]CYCLOHEXA 2,5 DIENONE; 4 [4 (4 TOLYLAMINO) 5 (4 TOLYLIMINO) 1,5 DIHYDRO 2H IMIDAZOL 2 YLIDENE]CYCLOHEXA 2,5 DIENETHIONE; 4 [4 (4 TOLYLAMINO) 5 (4 TOLYLIMINO) 1,5 DIHYDRO 2H IMIDAZOL 2 YLIDENE]CYCLOHEXA 2,5 DIENONE; 8 [5 (4 TOLYLAMINO) 4 (4 TOLYLIMINO) 4H IMIDAZOL 2 YL] 1 NAPHTHOIC ACID; CARBOXYLIC ACID; HYDROXIDE; IMIDAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; COLUMN CHROMATOGRAPHY; CYCLIZATION; HYDROPHILICITY; INFRARED SPECTROSCOPY; MASS SPECTROMETRY; OXIDATION REDUCTION REACTION; PROTON NUCLEAR MAGNETIC RESONANCE; SOLUBILITY;

EID: 53249123350     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1067249     Document Type: Article

References (22)

1. Matschke, M.; Beckert, R. Molecules 2007, 12, 723.
2. Blumhoff, J.; Beckert, R.; Walther, D.; Rau, S.; Rudolph, M.; Görls, H.; Plass, W. Eur. J. Inorg. Chem. 2007, 3, 481.
3. Matschke, M.; Käpplinger, C.; Weiß, D.; Beckert, R. Tetrahedron Lett. 2005, 46, 8249.
4. Matschke, M.; Käpplinger, C.; Weiß, D.; Albrecht, S.; Distler, W.; Beckert, R. DE 102,005,034,129, 2007.
5. Büchel, K. H.; Erdmann, H. Chem. Ber. 1976, 109, 1638.
6. Büchel, K. H.; Erdmann, H. Chem. Ber. 1977, 110, 3226.
7. Fabian, J.; Beckert, R.; Atzrodt, J. J. Prakt. Chem./Chem.-Ztg. 1997, 339, 735.
8. Atzrodt, J.; Brandenburg, J.; Käpplinger, C.; Beckert, R.; Günther, W.; Görls, H.; Fabian, J. J. Prakt. Chem./Chem.-Ztg. 1997, 339, 729.
9. Müller, D.; Beckert, R.; Görls, H. Synthesis 2001, 601.
10. Perry, C.; Parveen, Z. J. Chem. Soc., Perkin Trans. 2 2001, 512.
11. Bargellini, G. Gazz. Chim. Ital. 1904, 34/II, 455.
12. Hellwinkel, D.; Lenz, R.; Lammerzahl, F. Tetrahedron 1983, 39, 2073.
13. Zee-Cheng, R.; Cheng, C. J. Med. Chem. 1985, 28, 1216.
14. Bryce-Smith, D.; Gilbert, A.; McColl, I. S.; Drew, M. G.; Yianni, P. J. Chem. Soc., Perkin Trans. 1 1987, 1147.
15. Mullican, M.; Wilson, M.; Connor, D.; Kostlan, C.; Schrier, D.; Dyer, R. J. Med. Chem. 1993, 36, 1090.
16. Bis(alkylsulfanyl)quinomethides: Gompper, R.; Kutter, E. Chem. Ber. 1965, 98, 1374.
17. Gebauer, T.; Beckert, R.; Weiß, D.; Knop, K.; Käpplinger, C.; Görls, H. Chem. Commun. 2004, 1860.
18. Käpplinger, C.; Beckert, R.; Günther, W.; Görls, H. Liebigs Ann./Recl. 1997, 617.
19. Matschke, M.; Käpplinger, C.; Beckert, R. Tetrahedron 2006, 62, 8586.
20. Neidlein, R.; Hartz, G. Helv. Chim. Acta 1986, 69, 315.
21. Grossmann, N.; Wehner, V.; Weise, A.; Winning, B.; Fanghaenel, E. J. Prakt. Chem. 1988, 330, 204.
22. Xie, C.; Lahti, P. M. Tetrahedron Lett. 1999, 40, 4305.