title: Synthesis, reactions and antimicrobial activities of 8-ethoxycoumarin derivatives.
abstract: Condensation of 3-acetyl-8-ethoxycoumarin (3) with thiosemicarbazide gave ethylidenehydrazinecarbothioamide 5, which was transformed into the thiazolidin-4-one derivatives 6,7. Interaction of 3 with DMF/POCl(3) gave b-chloroacroline derivative 8. Treatment of 3 with malononitrile gave benzo[c]chromone and 2-aminobenzonitrile derivatives 9 and 10, respectively with respect to the reaction conditions. Condensation of 3-(2-bromoacetyl)-8-ethoxycoumarin (4) with o-phenylenediamine gave 3-(quioxaline-2-yl)-8-ethoxycoumarin hydrobromide (11), while 4 reacted with 2-aminopyridine to give chromenopyridopyrimidine derivative 12. Condensation of 4 with potassium thio-cyanate/methanol gave an unexpected derivative, 2H-chromeno-3-carboxy(methyl-carbonimidic)thioanhydride 16, which upon treatment with (NH(2))(2)·H(2)O gave 3-ethoxy-2-hydroxybenzaldehyde azine 19. Interaction of 4 with thiourea derivatives gave thiazole derivatives 20a-c. The structures of the newly synthesized compounds were confirmed by their spectra data. The newly synthesized compounds were also screened for their antimicrobial activity.
authors.affiliation: Chemistry Department, Faculty of Medicine, Jazan University, Jazan 82621, Saudi Arabia. hanysm83@yahoo.com
authors.forename: Hany M
authors.initials: HM
authors.lastname: Mohamed
authors.forename: Ashraf H F
authors.initials: AH
authors.lastname: Abd El-Wahab
authors.forename: Kamal A
authors.initials: KA
authors.lastname: Ahmed
authors.forename: Ahmed M
authors.initials: AM
authors.lastname: El-Agrody
authors.forename: Ahmed H
authors.initials: AH
authors.lastname: Bedair
authors.forename: Fathy A
authors.initials: FA
authors.lastname: Eid
authors.forename: Mostafa M
authors.initials: MM
authors.lastname: Khafagy
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D003374:Coumarins / Q000138:chemical synthesis* / Q000494:pharmacology; D003500:Cyclization; D006090:Gram-Negative Bacteria / Q000187:drug effects; D006094:Gram-Positive Bacteria / Q000187:drug effects; D006835:Hydrazones / Q000138:chemical synthesis / Q000494:pharmacology; D008826:Microbial Sensitivity Tests; D009570:Nitriles / Q000138:chemical synthesis / Q000494:pharmacology; D013844:Thiazoles / Q000138:chemical synthesis / Q000494:pharmacology; D013861:Thiocyanates / Q000138:chemical synthesis / Q000494:pharmacology; D044366:Transition Temperature
chemical_list: D000900:Anti-Bacterial Agents; D003374:Coumarins; D006835:Hydrazones; D009570:Nitriles; D013844:Thiazoles; D013861:Thiocyanates