Synthesis, Reactions and Antimicrobial Activities of 8-Ethoxycoumarin Derivatives

Molecules

Hany M. Mohamed¹  Ashraf H. F. Abd El-Wahab¹  Kamal A. Ahmed¹  Ahmed M. El-Agrody¹  Ahmed H. Bedair¹  Fathy A. Eid¹ 

[1]¹Chemistry Department, Faculty of Medicine, Jazan University, Jazan 82621, Saudi Arabia

关键词: 3-acetyl-8-ethoxycoumarin;    bromination;    active methylene;    thiazole derivatives;    thiosemicarbazide;    KSCN;    antimicrobial activities;   

DOI  :  10.3390/molecules17010971

来源: mdpi

【 摘 要 】

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.

【 授权许可】

CC BY   
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