Synthesis of Hydroxyquinoline Derivatives, Aminohydroxychromene, Aminocoumarin and Their Antibacterial Activities

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 viu Michael addition of different substituted aminonaphthol (1), aminophenol (6), resorcinol derivatives (15a-d), chloronaphthol (17) and 4-hydroxycoumarin (19) with a-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, 1 H NMR, 1 3 C 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).