An effective microwave-induced iodine-catalyzed method for the synthesis of quinoxalines via condensation of 1,2-diamines with 1,2-dicarbonyl compounds

Molecules

Volumn 15, Issue 6, 2010, Pages 4207-4212

  Bandyopadhyay, Debasish ^a   Mukherjee, Sanghamitra ^a   Rodriguez, Robert R ^a   Banik, Bimal K ^a  

^a UNIVERSITY OF TEXAS PAN AMERICAN   (United States)

Author keywords

Amines; Dicarbonyl compounds; Iodine; Microwave; Quinoxalines

Indexed keywords

DIAMINE; QUINOXALINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; MICROWAVE RADIATION; SYNTHESIS;

DIAMINES; MICROWAVES; MOLECULAR STRUCTURE; QUINOXALINES;

EID: 77954285103     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules15064207     Document Type: Article

References (15)

1. Hazeldine, S. T.; Polin, L.; Kushner, J.; Paluch, J.; White, K.; Edelstein, M.; Palomino, E.; Corbett, T. H.; Horwitz, J. P. Design, Synthesis, and Biological Evaluation of Analogues of the Antitumor Agent, 2-{4-[(7-Chloro-2-quinoxalinyl) oxy]phenoxy}propionic Acid (XK469). J. Med. Chem. 2001, 44, 1758-1776.
2. Seitz, L. E.; Suling, W. J.; Reynolds, R. C. Synthesis and Antimycobacterial Activity of Pyrazine and Quinoxaline Derivatives. J. Med. Chem. 2002, 45, 5604-5606.
3. Badran, M. M.; Botros, S.; El-Gendy, A. A.; Abdou, N. A.; El-Assi, H.; Salem, A. Part I: novel quinoxaline derivatives of biological interest. Bull. Pharm. Sci. 2001, 24, 135-144.
4. Bailly, C.; Echepare, S.; Gago, F.; Waring, M. J. Recognition elements that determine affinity and sequence-specific binding to DNA of 2QN, a biosynthetic bis-quinoline analogue of echinomycin. Anti Canc. Drug Des. 1999, 14, 291-303.
5. Sato, K.; Shiratori, O.; Katagiri, K. Mode of action of quinoxaline antibiotics. Interaction of quinomycin A with deoxyribonucleic acid. J. Antibiot. 1967, 20, 270-276.
6. Becker, F. F.; Banik, B. K. Polycyclic aromatic compounds as anticancer agents: synthesis and biological evaluation of some chrysene derivatives. Bioorg. Med. Chem. Lett. 1998, 8, 2877-2880.
7. Becker, F. F.; Mukhopadhyay, C.; Hackfeld, L.; Banik, I.; Banik, B. K. Polycyclic aromatic compounds as anticancer agents: synthesis and biological evaluation of dibenzofluorene derivatives. Bioorg. Med. Chem. 2000, 8, 2693-2699.
8. Banik, B. K.; Becker, F. F. Polycyclic aromatic compounds as anticancer agents. 4. Structureactivity relationships of chrysene and pyrene derivatives. Bioorg. Med. Chem. 2001, 9, 593-605.
9. Banik, B. K.; Becker, F. F. Synthesis, electrophilic substitution and structure-activity relationship studies of polycyclic aromatic compounds towards the development of anticancer agents. Curr. Med. Chem. 2001, 8, 1513-1533.
10. Banik, B. K.; Becker, F. F.; Banik, I. Synthesis of anticancer β-lactams: Mechanism of action. Bioorg. Med. Chem. 2004, 12, 2523-2528.
11. Banik, I.; Becker, F. F.; Banik, B. K. Stereoselective Synthesis of β-Lactams with Polyaromatic Imines: Entry to New and Novel Anticancer Agents. J. Med. Chem. 2003, 46, 12-15.
12. Kamal, A.; Reddy, K. L.; Devaiah, V.; Shankaraiah, N.; Rao, M. V. Recent advances in the solidphase combinatorial synthetic strategies for the quinoxaline, quinazoline and benzimidazole based privileged structures. Mini Rev. Med. Chem. 2006, 6, 71-89.
13. Srinivas, C.; Kumar, C. N. S. S. P.; Rao, V. J.; Palaniappan, S. Efficient, convenient and reusable polyaniline-sulfate salt catalyst for the synthesis of quinoxaline derivatives. J. Mol. Catal. A: Chem. 2007, 265, 227-230. (Pubitemid 46357017)
14. Zhou, J. F.; Gong, G. X.; Zhi, S. J.; Duan, X. L. Microwave-assisted catalyst-free and solvent-free method for the synthesis of quinoazlines. Synth. Commun. 2009, 39, 3743-3754.
15. More, S. V.; Sastry M. N. V.; Yao C.-F. Cerium (IV) ammonium nitrate (CAN) as a catalyst in tap water: A simple, proficient and green approach for the synthesis of quinoxalines. Green Chem. 2006, 8, 91-95.