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Synthesis, Reactions and Antimicrobial Activities of 8-Ethoxycoumarin Derivatives
Chemistry Department, Faculty of Medicine, Jazan University, Jazan 82621, Saudi Arabia
Chemistry Department, Faculty of Science, Jazan University, Jazan 2097, Saudi Arabia
Chemistry Department, Faculty of Science, Al-Azhar University, Nasr City, Cairo 11884, Egypt
Chemistry Department, Faculty of Science, King Khalid University, Abha 9004, Saudi Arabia
* Author to whom correspondence should be addressed.
Received: 14 November 2011; in revised form: 1 January 2012 / Accepted: 4 January 2012 / Published: 18 January 2012
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/POCl3 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 (NH2)2·H2O 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.
Keywords: 3-acetyl-8-ethoxycoumarin; bromination; active methylene; thiazole derivatives; thiosemicarbazide; KSCN; antimicrobial activities
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Mohamed, H.M.; El-Wahab, A.H.F.A.; Ahmed, K.A.; El-Agrody, A.M.; Bedair, A.H.; Eid, F.A.; Khafagy, M.M. Synthesis, Reactions and Antimicrobial Activities of 8-Ethoxycoumarin Derivatives. Molecules 2012, 17, 971-988.
Mohamed HM, El-Wahab AHFA, Ahmed KA, El-Agrody AM, Bedair AH, Eid FA, Khafagy MM. Synthesis, Reactions and Antimicrobial Activities of 8-Ethoxycoumarin Derivatives. Molecules. 2012; 17(1):971-988.
Mohamed, Hany M.; El-Wahab, Ashraf H. F. Abd; Ahmed, Kamal A.; El-Agrody, Ahmed M.; Bedair, Ahmed H.; Eid, Fathy A.; Khafagy, Mostafa M. 2012. "Synthesis, Reactions and Antimicrobial Activities of 8-Ethoxycoumarin Derivatives." Molecules 17, no. 1: 971-988.