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Paper | Regular issue | Vol 63, No. 8, 2004, pp.1793-1812
Published online, 25th June, 2004
DOI: 10.3987/COM-04-10089
Synthesis of Hydroxyquinoline Derivatives, Aminohydroxychromene, Aminocoumarin and Their Antibacterial Activities

Alaa S. Abd-El-Aziz,* Ahmed M. El-Agrody, Ahmed H. Bedair, T. Christopher Corkery, and Athar Ata

*Department of Chemistry, The University of Winnipeg, Winnipeg, Manitoba, R3B 2E9, Canada

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).