Synthesis of hydroxyquinoline derivatives, ...

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Title Synthesis of hydroxyquinoline derivatives, aminohydroxychromene, aminocoumarin and their antibacterial activities.
Author(s) Alaa S. Abd-El-Aziz, Ahmed M. El-Agrody, Ahmed H. Bedair, T. Christopher Corkery, Athar Ata
Journal Heterocycles,
Date 2004
Volume 63
Issue 8
Start page 1793
End page 1812
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).
DOI 10.3987/COM-04-10089

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