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Synthesis of Hydroxyquinoline Derivatives, Aminohydroxychromene, Aminocoumarin and Their Antibacterial Activities
Heterocycles (2004)
  • Ahmed M. El-Agrody, University of Winnipeg
  • Ahmed H. Bedair, University of Winnipeg
  • T. Christopher Corkery, University of Winnipeg
  • Athar Ata, University of Winnipeg
  • Alaa S. Abd-El-Aziz, University of Winnipeg
Abstract
Some new diaminochromenes (3a-f, 7a-c, and 10), 7-amino-4-aryl-coumarins (8a,b), 7-hydroxy-4-aryl-1,2-dihydroquinolines (9a-c) and 2-amino-7-hydroxy-4-(4-chlorophenyl)-4H-chromenes (16a-d) were synthesized via Michael addition of different substituted aminonaphthol (1), aminophenol (6), resorcinol derivatives (15a-d), chloronaphthol (17) and 4-hydroxycoumarin (19) with α-cyanocinnamonitriles (2a-c) and ethyl α-cyanocinnamate (2d-f). 2-Acetylamino-7-amino-4-(4-chlorophenyl)-4H-chromene-2-carbonitrile (14) was obtained as a unique product via hydrazinolysis of ethoxymethyleneamino derivative (13). The formation of coumarins (8a,b) and quinolines (9a-c) were anomalous case. Structures of the titled compounds cited in this article were elucidated by spectrometric data (IR, 1H NMR, 13C NMR (APT) and EMS). All of the newly synthesized compounds were evaluated for antimicrobial activities, where 16b and 16c exhibited activity against staphylococcus aureus (ATCC 25923).
Keywords
  • Hydroxyquinoline Derivative,
  • Amino-hydroxychromene,
  • Aminocoumarin,
  • Anti-bacterial,
  • Enaminonitrile
Disciplines
Publication Date
August 1, 2004
Citation Information
Ahmed M. El-Agrody, Ahmed H. Bedair, T. Christopher Corkery, Athar Ata, et al.. "Synthesis of Hydroxyquinoline Derivatives, Aminohydroxychromene, Aminocoumarin and Their Antibacterial Activities" Heterocycles Vol. 63 Iss. 8 (2004)
Available at: http://works.bepress.com/chriscorkery/13/