Sintesis Etil (E)-2-(3-(2-(2-((4-metil-2-okso-2H-kromen-7-il)oksi)asetil)hidrazineilidena)-2-oksoindolin-1-il)asetat

Susatyo, Alfin Yassar (2024) Sintesis Etil (E)-2-(3-(2-(2-((4-metil-2-okso-2H-kromen-7-il)oksi)asetil)hidrazineilidena)-2-oksoindolin-1-il)asetat. Other thesis, Institut Teknologi Sepuluh Nopember.

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Abstract

Senyawa 2H-kromen-2-on atau kumarin merupakan senyawa heterosiklik yang terdiri dari cincin benzen dan piron yang menyatu, kumarin beserta turunannya menunjukkan aktivitas biologis yang beragam. Senyawa 7-hidroksi-4-metil-2H-kromen-2-on 8 dengan kerangka kumarin juga memiliki aktivitas antivirus, antidiabet, serta antiinflamasi. Modifikasi struktur 7-hidroksi-4-metil-2H-kromen-2-on 8 dilakukan melalui alkilasi dan hidroksilasi pada posisi C4 dan C7. Penelitian ini bertujuan untuk mendapatkan (E)-2-(3-(2-(2-((4-metil-2-okso-2H-kromen-7-il)oksi)asetil)hidrazineilidena)-2-oksoindolin-1-il)asetat 1 melalui modifikasi 7-hidroksi-4-metil-2H-kromen-2-on 8 melalui alkilasi, substitusi dengan amina, dan substitusi oleh etil 2-(2,3-dioksoindolin-1-il)asetat 3. Penelitian dilakukan melalui sintesis 7-hidroksi-4-metil-2H-kromen-2-on 8, etil 2-((4-metil-2-okso-2H-kromen-7-il)oksi)asetat 7, etil 2-(2,3-dioksoindolin-1-il)asetat 3 dan 2-((4-metil-2-okso-2H-kromen-7-il)-oksi)asetohidrazida 2 yang dilanjutkan dengan reaksi pembentukan senyawa etil (E)-2-(3-(2-(2-((4-metil-2-okso-2H-kromen-7-il)oksi)asetil)hidrazineilidena)-2-oksoindolin-1-il)asetat 1. Penelitian yang dilakukan telah berhasil mendapatkan 7-hidroksi-4-metil-2H-kromen-2-on 8 dengan persen yield 99% melalui reaksi antara resorcinol 9 dalam etil asetoasetat 10. Etil 2-((4-metil-2-okso-2H-kromen-7-il)oksi)asetat 7 telah diperoleh dengan persen yield 56% melalui alkilasi 7-hidroksi-4-metil-2H-kromen-2-on 8 dengan etil kloroasetat 5. Senyawa 2-((4-metil-2-okso-2H-kromen-7-il)oksi)asetohidrazida 2 dengan diperoleh dengan persen yield 76% melalui reaksi etil 2-((4-metil-2-okso-2H-kromen-7-il)oksi)asetat 7 dengan hidrazin hidrat 6. Selanjutnya etil 2-(2,3-dioksoindolin-1-il)asetat 3 telah berhasil disintesis dengan persen yield 75% melalui reaksi isatin 4 dan etil kloroasetat 5. Akhirnya, etil (E)-2-(3-(2-(2-((4-metil-2-okso-2H-kromen-7-il)oksi)asetil)hidrazineilidena)-2-oksoindolin-1-il)asetat 1 telah berhasil diperoleh dengan persen yield 57% melalui reaksi 2-((4-metil-2-okso-2H-kromen-7-il)oksi)asetohidrazida 2 dengan etil 2-(2,3-dioksoindolin-1-il)asetat 3 dalam suasana asam.
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2H-chromen-2-one compounds or coumarins are heterocyclic compounds consisting of benzene and pyroon rings that are fused, coumarin and its derivatives show diverse biological activities. The compound 7-hydroxy-4-methyl-2H-chromene-2-on¬ 8 with a coumarin skeleton also has antiviral, antidiabetic, and anti-inflammatory activities. The structural modification of 7-hydroxy-4-methyl-2H-chromen-2-on¬ 8 is carried out through alkylation and hydroxylation at the C4 and C7 positions. This study aims to obtain (E)-2-(3-(2-(2-((4-methyl-2-oxo-2H-chromen-7-yl)oxy)acetyl)hydrrazineylidena)-2-oxoindolin-1-yl)acetate 1 through modification of 7-hydroxy-4-methyl-2H-chromen-2-on 8 through alkylation, substitution with amines, and substitution by ethyl 2-(2,3-dioxoindolin-1-yl)acetate 3. The research was carried out through the synthesis of 7-hydroxy-4-methyl-2H-chromen-2-on 8, ethyl 2-((4-methyl-2-oxo-2H-chromen-7-yl)oxy)acetate 7, ethyl 2-(2,3-dioxoindolin-1-yl)acetate 3 and 2-((4-methyl-2-oxo-2H-chromen-7-yl)-oxy)acetohydride 2 which was followed by the reaction of forming ethyl (E)-2-(3-(2-(2-((4-methyl-2-oxo-2H-chromen-7-yl)oxy)acetyl)hydrazineylidena)-2-oxoindolin-1-yl)acetate 1. The research conducted has succeeded in obtaining 7-hydroxy-4-methyl-2H-chromen-2-on 8 with a yield of 99% through the reaction between resorcinol 9 in ethyl acetoacetate 10. Ethyl 2-((4-methyl-2-oxo-2H-chromen-7-yl)oxy) acetate 7 has been obtained with a 56% yield by alkylation of 7-hydroxy-4-methyl-2H-chromen-2-on 8 with ethyl chloroacetate 5. Compound 2-((4-methyl-2-oxo-2H-chromen-7-yl)oxy)acetohydride 2 obtained with a yield of 76% through the reaction of ethyl 2-((4-methyl-2-oxo-2H-chromen-7-yl)oxy) acetate 4 with hydrazine hydrate 6. Furthermore, ethyl 2-(2,3-dioxoindolin-1-yl)acetate 3 has been successfully synthesized with a yield of 75 % through the reaction of isatin 4 and ethyl chloroacetate 5. Finally, ethyl (E)-2-(3-(2-(2-((4-methyl-2-oxo-2H-chromen-7-yl)oxy)acetyl)hydrazineylidena)-2-oxoindolin-1-yl)acetate 1 has been successfully obtained with a yield of 57% through the reaction of 2-((4-methyl-2-oxo-2H-chromen-7-yl)oxy)acetohydride 2 with ethyl 2-(2,3-dioxoindolin-1-yl)acetate 3 in an acidic enviroment.

Item Type:	Thesis (Other)
Uncontrolled Keywords:	kumarin, isatin, 7-hidroksi-4-metil-2H-kromen-2-one, alkilasi, coumarin, 7-hydroxy-4-methyl-2H-chromen-2-one, alkylation
Subjects:	Q Science > QD Chemistry > QD251.2 Chemistry, Organic. Biochemistry Q Science > QD Chemistry > QD341 Coumarins Q Science > QD Chemistry > QD471 Chemical compounds - Structure and formulas Q Science > QD Chemistry > QD481 Chemical structure.
Divisions:	Faculty of Science and Data Analytics (SCIENTICS) > Chemistry > 47201-(S1) Undergraduate Thesis
Depositing User:	Alfin Yassar Susatyo
Date Deposited:	27 Aug 2024 02:31
Last Modified:	27 Aug 2024 02:31
URI:	http://repository.its.ac.id/id/eprint/114811

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