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• Mohamed, H
• El-Wahab, A
• Ahmed, K
• El-Agrody, A
• Bedair, A
• Eid, F
• Khafagy, M
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• Mohamed, H
• El-Wahab, A
• Ahmed, K
• El-Agrody, A
• Bedair, A
• Eid, F
• Khafagy, M
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• El-Wahab, A
• Ahmed, K
• El-Agrody, A
• Bedair, A
• Eid, F
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Molecules 2012, 17(1), 971-988; doi:10.3390/molecules17010971

Article

Synthesis, Reactions and Antimicrobial Activities of 8-Ethoxycoumarin Derivatives

Hany M. Mohamed ^1,3,* , Ashraf H. F. Abd El-Wahab ^2,3 , Kamal A. Ahmed ³ , Ahmed M. El-Agrody ^3,4 , Ahmed H. Bedair ³ , Fathy A. Eid ³  and Mostafa M. Khafagy ³

¹ Chemistry Department, Faculty of Medicine, Jazan University, Jazan 82621, Saudi Arabia ² Chemistry Department, Faculty of Science, Jazan University, Jazan 2097, Saudi Arabia ³ Chemistry Department, Faculty of Science, Al-Azhar University, Nasr City, Cairo 11884, Egypt ⁴ 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

(This article belongs to the Special Issue Heterocycles)

Download PDF Full-Text [809 KB, uploaded 18 January 2012 11:54 CET]

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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