Sintesis 4-Metil-7-((5-(Metiltio)-1,3,4-Oksadiazol-2-il)Metoksi)-2H-Kromen-2-on

Trisnaningtyas, Andriany (2023) Sintesis 4-Metil-7-((5-(Metiltio)-1,3,4-Oksadiazol-2-il)Metoksi)-2H-Kromen-2-on. Other thesis, Institut Teknologi Sepuluh Nopember.

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Abstract

Kumarin (1, 2H-kromen-2-on) yang berupa cincin benzena yang bergabung dengan cincin 2-piron termasuk dalam senyawa flavonoid yang ditemukan dalam berbagai tanaman dan menunjukkan aktivitas biologis yang beragam. Senyawa 7-hidroksi-4-metil-2H-kromen-2-on 2 merupakan salah satu turunan kumarin 1 yang banyak dikaji dalam pengembangan berbagai senyawa aktif. Penelitian ini melaporkan sintesis turunan 7-hidroksi-4-metil-2H-kromen-2-on 2 dengan substituen 1,3,4-oxadiazola 9 berupa 4-metil-7-((5-(metiltio)-1,3,4-oksadiazol-2-il)metoksi)-2H-kromen-2-on 14. Sintesis senyawa 14 diawali dengan reaksi antara resorcinol 23 dan etil asetoasetat 22 yang menghasilkan senyawa 7-hidroksi-4-metil-2H-kromen-2-on 2 dengan yield 67,67%, Reaksi substitusi gugus hidroksil dari senyawa 7-hidroksi-4-metil-2H-kromen-2-on 2 oleh etil kloroasetat 21 menghasilkan etil 2-((4-metil-2-okso-2H-kromen-7-il)oksi)asetat 20 dengan yield 68,97%. Selanjutnya, substitusi gugus ester pada senyawa 20 dengan hidrazin hidrat 19 memberikan 2-((4-metil-2-okso-2H-kromen-7-il)oksi)asetohidrazida 18 dengan yield 94,54%. Pembentukan siklik 1,3,4-oxadiazola terjadi antara senyawa 18 dengan karbon disulfida 17 yang menghasilkan 7-((5-merkapto-1,3,4-oksadiazol-2-il)metoksi)-4-metil-2H-kromen-2-on 16 dengan yield 30,86%. Metilasi senyawa 16 oleh metil iodida 15 pada tahap akhir memberikan 4-metil-7-((5-(metiltio)-1,3,4-oksadiazol-2-il)metoksi)-2H-kromen-2-on 14 dengan yield 46,70%.
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Coumarin (1, 2H-chromen-2-one) is a heterocyclic compound consisting of a benzene ring and a 2-pyrone ring. 2H-chromen-2-one 1 and its derivatives exhibit diverse biological activities. Compound 7-hydroxy-4-methyl-2H-chromen-2-one 2 is one of the derivatives of coumarin 1 and reported to have potential as an antitumor, choleric, and antispasmodic agent. Structural modifications of 7-hydroxy-4-methyl-2H-chromen-2-one 2 can be achieved through alkylation and hydroxylation at positions C4 and C7. This research was conducted to obtain derivatives of 7-hydroxy-4-methyl-2H-chromen-2-one 2 with a 1,3,4-oxadiazole 9 substituent, namely 4-methyl-7-((5-(methylthio)-1,3,4-oxadiazol-2-yl)methoxy)-2H-chromen-2-one 14. The synthesis of compound 14 began with the synthesis of compound 7-hydroxy-4-methyl-2H-chromen-2-one 2 from resorcinol 23 and ethyl acetoacetate 22 with a yield of 67,67%, followed by the substitution reaction of the hydroxyl group of 7-hydroxy-4-methyl-2H-chromen-2-one 2 by ethyl chloroacetate 21, resulting in ethyl 2-((4-methyl-2-oxo-2H-chromen-7-yl)oxy)acetate 20 with a yield of 68,97%. The subsequent reaction involved compound 14 with hydrazine hydrate 19, resulting in 2-((4-methyl-2-oxo-2H-chromen-7-yl)oxy)acetohydrazide 18 with a yield of 94,54%. The cyclic formation of 1,3,4-oxadiazole 9 was performed between compound 18 and carbon disulfide 17, resulting in 7-((5-mercapto-1,3,4-oxadiazol-2-yl)methoxy)-4-methyl-2H-chromen-2-one 16 with a yield of 30,86%. The methylation of compound 16 with methyl iodide 15 gave 4-methyl-7-((5-(methylthio)-1,3,4-oxadiazol-2-yl)methoxy)-2H-chromen-2-one 14 with a yield of 46,70%.

Item Type:	Thesis (Other)
Uncontrolled Keywords:	kumarin, 1,3,4-Oxadiazola, karbon disulfida, coumarin, 1,3,4-Oxadiazole, carbon disulfide.
Subjects:	Q Science > QD Chemistry > QD251.2 Chemistry, Organic. Biochemistry Q Science > QD Chemistry > QD341 Coumarins
Divisions:	Faculty of Science and Data Analytics (SCIENTICS) > Chemistry > 47201-(S1) Undergraduate Thesis
Depositing User:	Andriany Trisnaningtyas
Date Deposited:	10 Aug 2023 02:11
Last Modified:	10 Aug 2023 02:11
URI:	http://repository.its.ac.id/id/eprint/104083

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