Sintesis N'-Benzilidena-2-((4-metil-2-okso-2H-kromen-7-il)oksi)asetohidrazida

Seviani, Winda (2023) Sintesis N'-Benzilidena-2-((4-metil-2-okso-2H-kromen-7-il)oksi)asetohidrazida. Other thesis, Institut Teknologi Sepuluh Nopember.

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Abstract

Senyawa 2H-kromen-2-on atau kumarin merupakan senyawa heterosiklik yang mengandung satu atom oksigen dan beserta turunannya menunjukkan aktivitas biologis yang beragam. Senyawa 7-hidroksi-4-metil-2H-kromen-2-on 6 dengan kerangka kumarin juga memiliki aktivitas antivirus terhadap hepatitis B, infeksi virus hepatitis C, dan HIV serta telah digunakan dalam penanganan penyakit alzheimer. Modifikasi struktur 7-hidroksi-4-metil-2H-kromen-2-on 6 dapat dilakukan melalui alkilasi dan hidroksilasi pada posisi C4 dan C7 dan dilaporkan dapat meningkatkan aktivitas biologi. Penelitian yang dilakukan bertujuan untuk mendapatkan N’-benzilidena-2-((4-metil-2-okso-2H-kromen-7-il)oksi)asetohidrazida 1 melalui modifikasi 7-hidroksi-4-metil-2H-kromen-2-on 6 melalui alkilasi, insersi amina, dan substitusi benzaldehida. Penelitian dilakukan melalui sintesis 7-hidroksi-4-metil-2H-kromen-2-on 6, etil 2-((4-metil-2-okso-2H-kromen-7-il)oksi)asetat 4, dan 2-((4-metil-2-okso-2H-kromen-7-il)oksi)asetohidrazida 2 yang dilanjutkan dengan reaksi pembentukan senyawa benzilidena. Penelitian yang dilakukan telah berhasil mendapatkan 7-hidroksi-4-metil-2H-kromen-2-on 6 dengan rendemen 63,82% melalui reaksi antara resorcinol 8 dalam etil asetoasetat 9. Etil 2-((4-metil-2-okso-2H-kromen-7-il)oksi)asetat 4 dengan rendemen 57,40% telah diperoleh melalui alkilasi 7-hidroksi-4-metil-2H-kromen-2-on 6 dengan etil kloroasetat 7 dalam suasana basa (penambahan K2CO3). Selanjutnya, 2-((4-metil-2-okso-2H-kromen-7-il)oksi)asetohidrazida 2 dengan rendemen 94,86% diperoleh melalui reaksi etil 2-((4-metil-2-okso-2H-kromen-7-il)oksi)asetat 4 dengan hidrazin hidrat 5. Akhirnya, N’-benzilidena-2-((4-metil-2-okso-2H-kromen-7-il)oksi)asetohidrazida 1 dengan rendemen 79,23% telah berhasil diperoleh melalui reaksi 2-((4-metil-2-okso-2H-kromen-7-il)oksi)asetohidrazida 2 dengan benzaldehida 3 dalam suasana asam.
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The 2H-chromen-2-one or coumarin compound is a heterocyclic compound containing one atom of oxygen and its derivatives show various biological activities. The 7-hydroxy-4-methyl-2H-chromen-2-one 6 compound with a coumarin framework also has antiviral activity against hepatitis B, hepatitis C virus infection, and HIV and has been used in the treatment of Alzheimer's disease. Modification of the 7-hydroxy-4-methyl-2H-chromen-2-one 6 structure can be carried out through alkylation and hydroxylation at the C4 and C7 positions and is reported to increase biological activity. The aim of the research was to obtain N'-benzylidene-2-((4-methyl-2-oxo-2H-chromen-7-yl)-oxy)acetohydrazide 1 through modification of 7-hydroxy-4-methyl-2H-chromen-2-one 6 via alkylation, amine insertion, and benzaldehyde substitution. The research was carried out through the synthesis of 7-hydroxy-4-methyl-2H�chromen-2-one 6, ethyl 2-((4-methyl-2-oxo-2H-chromen-7-yl)oxy)acetate 4, and ethyl 2-((4-methyl-2-oxo-2H-chromen-7-yl)oxy)acetohydrazide 2 followed by the reaction to form a benzylidene compound. The research has succeeded in obtaining 7-hydroxy-4-methyl-2H-chromen-2-one 6 with a yield of 63.82% through the reaction between resorcinol 8 in ethyl acetoacetate 9. Ethyl 2-((4-methyl-2-oxo-2H-chromen-7-yl)oxy)acetate 4 in a yield of 57.40% was obtained by alkylation of 7-hydroxy-4-methyl-2H-chromen-2-one 6 with ethyl chloroacetate 7 in alkaline conditions (addition of K2CO3). Furthermore, 2-((4-methyl-2-oxo-2H-chromen-7-yl)oxy)acetohydrazide 2 with a yield of 94.86% was obtained through the reaction of ethyl 2-((4-methyl-2-oxo-2H-chromen-7-yl)oxy)acetate 4 with hydrazine hydrate 5. Finally, N'-benzylidene-2-((4-methyl-2-oxo-2H-chromen-7-yl)oxy)acetohydrazide 1 with yield 79.23% was successfully obtained by the reaction of 2-((4-methyl-2-oxo-2H-chromen-7- yl)oxy)acetohydrazide 2 with benzaldehyde 3 in an acidic conditions.

Item Type:	Thesis (Other)
Uncontrolled Keywords:	coumarin, 7-hydroxy-4-methyl-2H-chromen-2-one, benzaldehyde, benzylidenekumarin, 7-hidroksi-4-metil-2H-kromen-2-on, benzaldehida, benzilidena
Subjects:	Q Science > QD Chemistry > QD251.2 Chemistry, Organic. Biochemistry
Divisions:	Faculty of Science and Data Analytics (SCIENTICS) > Chemistry > 47201-(S1) Undergraduate Thesis
Depositing User:	Winda Seviani
Date Deposited:	17 Feb 2023 10:27
Last Modified:	17 Feb 2023 10:27
URI:	http://repository.its.ac.id/id/eprint/97464

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