Synthesis, characterization and antibacterial activity of some novel azo-azoimine dyes of 6-bromo-2-naphthol

International Journal of ChemTech Research

Volumn 2, Issue 3, 2010, Pages 1823-1830

  Chopde, Himani N ^a   Meshram, Jyotsna S ^a   Pagadala, Ramakanth ^a   Mungole, Arvind J ^a  

^a RTM NAGPUR UNIVERSITY   (India)

Author keywords

Antimicrobial activities; Azo dyes; Betti's condensation reaction

Indexed keywords

1 ((ARYLBENZYLIDENEAMINO)(ARYLPHENYL)METHYL) 6 BROMO NAPHTHALEN 2 OL; 1 ((BENZYLIDENEAMINO)(PHENYL)METHYL) 6 BROMO 3 ((4 NITROPHENYL)DIAZENYL) NAPHTHALEN 2 OL; 6 BROMO 1 ((2 CHLOROBENZYLIDENEAMINO)(2 CHLOROPHENYL)METHYL) 3 ((4 NITROPHENYL)DIAZENYL)NAPTHALEN 2 OL; 6 BROMO 1 ((2 HYDROXYBENZYLIDENEAMINO)(2 HYDROXYPHENYL)METHYL) 3 ((4 NITROPHENYL)DIAZENYL) NAPHTHALEN 2 OL; 6 BROMO 1 ((2 NITROBENZYLIDENEAMINO)(2 NITROPHENYL)METHYL) 3 ((4 NITROPHENYL) DIAZENYL)NAPHTHALEN 2 OL; 6 BROMO 1 ((3 BROMOBENZYLIDENEAMINO)(3 BROMOPHENYL)METHYL) 3 ((4 NITROPHENYL)DIAZENYL)NAPHTHALEN 2 OL; 6 BROMO 1 ((3 NITROBENZYLIDENEAMINO)(3 NITROPHENYL)METHYL) 3 ((4 NITROPHENYL)DIAZENYL)NAPHTHALEN 2 OL; 6 BROMO 1 ((4 (DIMETHYLAMINO)BENZYLIDENEAMINO)(4 (DIMETHYLAMINO)PHENYL)METHYL 3 ((4 NITROPHENYL)DIAZENYL) NAPHTHALEN 2 OL; 6 BROMO 1 ((4 CHLOROBENZYLIDENEAMINO)(4 CHLOROPHENYL)METHYL) 3 ((4 NITROPHENYL) DIAZENYL)NAPHTHALEN 2 OL; 6 BROMO 1 ((4 HYDROXYBENZYLIDENEAMINO)(4 HYDROXYPHENYL)METHYL) 3 ((4 NITROPHENYL)DIAZENYL)NAPHTHALEN 2 OL; 6 BROMO 1 (FURAN 2 YL(FURAN 2 YLMETHYLENEAMINO)METHYL) 3 ((4 NITROPHENYL)DIAZENYL)NAPHTHALEN 2 OL; AMMONIA; BASE; DYE; IMINE; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ARTICLE; DIAZOTIZATION; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; IN VITRO STUDY; INFRARED SPECTROSCOPY; MASS SPECTROMETRY; NONHUMAN; ONE POT SYNTHESIS; POLYMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 77957328870     PISSN: None     EISSN: 09744290     Source Type: Journal    
DOI: None     Document Type: Article

References (33)

1. Betti M., Condensation between {open box}-naphthol, aldehydes and amines, J. Chem. Soc., 1901, 80(1), 81-82.
2. Smith E. H. and Cooper E. N., Ring-Chain Tautomerism of Derivatives of 1-(a- Aminobenzy1)-naphthol with Aromatic Aldehydes, J. Org. Chem., 1970, 36(7).
3. Pirrone F., Hydroxyquinolines. V. Amino derivatives of 7-benzyl-8-hydroxyquinoline.7-[a- (p-nitroanilino)benzyl]-8-hydroxyquinoline, Gazzetta Chimica Italiana, 1940, 70, 520-527.
4. Phillips J. P. and Barrall E. M., Betti reactions of some phenols, J. Org. Chem., 1956, 21, 692-694.
5. Phillips J. P., The reactions of 8-quinolinol, Chem. Rev. 1956, 56, 271-297.
6. Brode W. R. and Littman J. B., Condensations of secondary amines with aldehydes and naphthols, J. Amer. Chem. Soc., 1930, 52, 1655-1659.
7. Wang Y., Li X. and Ding K., Synthesis of a new type of chiral amino phosphine ligands for asymmetric catalysis, Tetrahedron Asymm., 2002, 13, 1291-1297.
8. Cardellicchio C., Ciccarella G., Naso F., Perna F. and Tortorella P., Use of readily available chiral compounds related to the Betti base in the enantioselective addition of diethylzinc to aryl aldehydes, Tetrahedron, 1999, 55, 14685-14692.
9. Szatmari I., Tamas A., Martinek L. and Fulop F., Substituent effects in the ring-chain tautomerism of 1, 3-diaryl-2, 3-dihydro-1H-naphth[1, 2-e] [1, 3]oxazines, Tetrahedron, 2003, 59, 2877-2884.
10. Grumbach H. J., Arend M. and Risch N., Aminoalkylation of electron-rich aromatic compounds using preformed iminium salts derived from aldehydes other than formaldehyde, Synth., 1996, 883-887.
11. Szatmari I., Heteny A., Lazar L. and Fulop F., Transformation reactions of the Betti base analog aminonaphthols, J. Heterocycl. Chem., 2004, 41, 367-373.
12. Heydenreich M., Koch A., Klod S., Szatmari I., Fulop F. and Kleinpeter. E, Synthesis and conformational analysis of napht[10, 20: 5, 6][1, 3]oxazino[3, 2-c][1, 3]benzoxazine and napht [10, 20: 5, 6] [1, 3] oxazino [3, 4-c][1, 3] benzoxazine derivatives, Tetrahedron, 2006, 62, 11081-11089.
13. Palmieri G., A practical o-hydroxybenzylamines promoted enantioselective addition of dialkylzincs to aldehydes with asymmetricamplification, Tetrahedron Asymm., 2000, 11, 3361-3373.
14. Ma F., Ai L., Shen X. and Zhang C., New macrocyclic compound as chiral shift reagent for carboxylic acids, Org. Lett., 2007, 9, 125-127.
15. Lu J., Xu X., Wang C., He J., Hu Y. and Hu H., Synthesis of chiral ligands derived from the Betti base and their use in the enantioselective addition of diethyl zinc to aromatic aldehydes, Tetrahedron Lett. 2002, 43, 8367-8369.
16. Poel H. V., Guilaumet G. and Massuard V. M., Synthesis of 6, 7, 8, 9-tetrahydropyrido [2, 3-b]indolizine and 3, 4-dihydro-2Hpyrido[ 20, 30: 4, 5]pyrrolo- [2, 1-b] [1, 3] oxazine derivatives as new melatonin receptor ligands, Tetrahedron Lett., 2002, 43, 1205-1208.
17. Zang P., Terefenko E. A., Fensome A., Wrobel J., Winneker R. and Zang Z., Novel 6-aryl-1, 4-dihydrobenzo[d]oxazine-2-thiones as potent, selective, and orally active nonsteroidal progesterone receptor agonists, Bioorg. Med. Chem. Lett., 2003, 13, 1313-1316.
18. Bakhsh and Rufchahi, Synthesis, characterization and spectroscopic properties of some new azo dyes derived from 6-aminopyrimidine-2, 4(1H, 3H) - dione, Orient. J. Chem., 2009, 25, 41-45.
19. Naik A. P., Desai K. R. and Patel H. S., Synthesis of azo dyes based on alpha-Naphtholformaldehyde oligomer and their application on textile, Iran. Poly. J., 2001, 10, 1-7.
20. Jarrahpour A. A., Motamedifar M., Pakshir K., Hadi N. and Zarei M., Synthesis of Novel Azo Schiff Bases and Their Antibacterial and Antifungal Activities, Molecules, 2004, 9, 815-824.
21. More P. G., Bhalvankar R. B. and Pattar S. C., Synthesis and biological activities of Schiff bases of aminothiazoles, J. Ind. Chem. Soc., 2001, 78, 474-475.
22. El-Masry A. H., Fahmy H. H. and Abdelwahed S. H. A., Synthesis and antimicrobial Activity of Some New Benzimidazole Derivatives, Molecules, 2000, 5, 1429-1438.
23. Baseer M. A., Jadhav V. D., Phule R. M., Archana Y. V. and Vibhute Y. B., Synthesis and antimicrobial activity of some new Schiff bases, Orient. J. Chem., 2000, 16, 553-556.
24. Pandeya S. N., Sriram D., Nath G. and DeClercq E., Synthesis and antimicrobial activity of Schiff and mannich bases of isatin and its derivatives with pyrimidine. Farmaco., 1999, 54, 624-628.
25. Singh W. M. and Dash B. C., Synthesis of some new Schiff bases containing thiazole and oxazole nuclei and their fungicidal activity, Pesticides, 1988, 22, 33-37.
26. Hodnett E. M. and Dunn W. J., Structureantitumour activity correlation of some Schiff bases, J. Med. Chem., 1970, 13, 768-770.
27. Desai S. B., Desai P. B. and Desai. K. R., Synthesis of some Schiff bases, thiazolidones, and azetidinones derived from 2, 6-diaminobenzo[1, 2-d: 4, 5-d']bisthiazole and their anticancer activities, Heterocycl. Commun., 2001, 7, 83-90.
28. Pathak P., Jolly V. S. and Sharma K. P., Synthesis and biological activities of some new substituted arylazo Schiff bases, Orient. J. Chem., 2000, 16, 161-162.
29. Samadhiya S. and Halve A., Synthetic utility of Schiff bases as potential herbicidal agents, Orient. J. Chem., 2001, 17, 119-122.
30. Taggi A. E., Hafez A. M., Wack H., Young B., Ferraris D. and Lectka T., The development of the first catalysed reaction of ketenes and imines: catalytic asymmetric synthesis of lactams, J. Amer. Chem. Soc., 2002, 124, 6626-6635.
31. Aydogan F., Ocal N., Turgut Z. and Yolacan C., Transformations of aldimines derived from pyrrole-2-carboxaldehyde. Synthesis of thiazolidino-fused compounds, Bull. Korean. Chem. Soc., 2001, 22, 476-480.
32. Khandar A. A., Nejati K. and Rezvani Z., Synthesis, Characterization and Study of the Use of Cobalt (II) Schiff-Base Complexes as Catalysts for the Oxidation of Styrene by Molecular Oxygen, Molecules, 2005, 10, 302-311.
33. Namkung M. J. and Fletcher T. L., Derivatives of 2-Hydroxy-p-Phenetidine. I. Azomethines, J. Med. Chem., 1970, 13, 329-332.