European Journal of Chemistry 2017, 8(4), 417-421. doi:10.5155/eurjchem.8.4.417-421.1659

Reactions of 5-(4-methoxy-3-methylphenyl)-2(3H)-furanone with some electrophilic and nucleophilic reagents


Mohamed Helmy Abd El-hamied Soliman (1) , Sahar Said Ahmed El-Sakka (2,*)

(1) Chemistry Department, Faculty of Science, Suez University, Suez, 43527, Egypt
(2) Chemistry Department, Faculty of Science, Suez University, Suez, 43527, Egypt
(*) Corresponding Author

Received: 11 Oct 2017, Accepted: 05 Nov 2017, Published: 31 Dec 2017

Abstract


5-(4-Methoxy-3-methylphenyl)-2(3H)-furanone was prepared and reacted with some nucleophilic and electrophilic reagents. The condensation of furanone with aromatic aldehydes or phthalic anhydride yielded the corresponding 3-arylidenefuranone derivatives and phthalide, respectively. While the treatment of furanone with amines in refluxing ethanol led to the formation of amides. The reaction of the amides with thionyl chloride afforded the corresponding isothiazolones. The benzimidazole derivative was prepared via the reaction of the 2(3H)-furanone with o-phenylenediamine in boiling ethanol. However, hydrazine hydrate affected ring opening of furanone to give the corresponding acid hydrazide, which underwent in situ cyclization into the corresponding pyridazinone. The base catalyzed ethanolysis of furanone afforded the corresponding ethyl ester.


Keywords


Isothiazolone; Pyridazinone; 2(3H)-Furanone; 4-Oxobutanamide; o-Phenylenediamine; Condensation reaction

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DOI: 10.5155/eurjchem.8.4.417-421.1659

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How to cite


Soliman, M.; El-Sakka, S. Eur. J. Chem. 2017, 8(4), 417-421. doi:10.5155/eurjchem.8.4.417-421.1659
Soliman, M.; El-Sakka, S. Reactions of 5-(4-methoxy-3-methylphenyl)-2(3H)-furanone with some electrophilic and nucleophilic reagents. Eur. J. Chem. 2017, 8(4), 417-421. doi:10.5155/eurjchem.8.4.417-421.1659
Soliman, M., & El-Sakka, S. (2017). Reactions of 5-(4-methoxy-3-methylphenyl)-2(3H)-furanone with some electrophilic and nucleophilic reagents. European Journal of Chemistry, 8(4), 417-421. doi:10.5155/eurjchem.8.4.417-421.1659
Soliman, Mohamed, & Sahar Said Ahmed El-Sakka. "Reactions of 5-(4-methoxy-3-methylphenyl)-2(3H)-furanone with some electrophilic and nucleophilic reagents." European Journal of Chemistry [Online], 8.4 (2017): 417-421. Web. 21 Sep. 2019
Soliman, Mohamed, AND El-Sakka, Sahar. "Reactions of 5-(4-methoxy-3-methylphenyl)-2(3H)-furanone with some electrophilic and nucleophilic reagents" European Journal of Chemistry [Online], Volume 8 Number 4 (31 December 2017)

DOI Link: https://doi.org/10.5155/eurjchem.8.4.417-421.1659

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