Sintesis Empat Hidrazona Dari 5-Metilisatin dan 5-Nitroisatin

Fahmi, M. Riza Ghulam (2015) Sintesis Empat Hidrazona Dari 5-Metilisatin dan 5-Nitroisatin. Undergraduate thesis, Institut Teknologi Sepuluh Nopember.

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Abstract

Isatin merupakan prekursor untuk sintesis senyawa organik, seperti hidrazona. Hidrazona dengan gugus azometin memiliki bioaktivitas sebagai antibakteri. Modifikasi baru dari turunan hidrazona yaitu 2-tiofenakarbonilhidrazon-5-nitroisatin (8b), 2- tiofenakarbonilhidrazon-5-metilisatin (8a), 2- tiofenakarbonilhidrazon-(N-metil)-5-metilisatin (11a), dan 2- tiofenakarbonilhidrazon-(N-metil)-5-nitroisatin (11b) telah disintesis. Reaksi antara 5-metilisatin (9a) dan 5-nitroisatin (9b) dengan asam 2-tiofenakarboksilat hidrazida dalam pelarut etanol dengan katalis asam sulfat dihasilkan 2-tiofenakarbonilhidrazon- 5-metilisatin (8a) dan 2-tiofenakarbonilhidrazon-5-nitroisatin (8b) dengan rendeman 75% dan 83%. Metilasi dari 5-metilisatin (9a) dan 5-nitroisatin (9b) menghasilkan (N-metil)-5-metilisatin (12a) dan (N-metil)-5-nitroisatin (12b) dengan rendemen 76% dan 89%, yang kemudian direaksikan dengan asam 2- tiofenakarboksilat hidrazida diperoleh masing-masing rendemen 57% dan 87%. Struktur dari hasil sintesis dikarakterisasi menggunakan uji titik leleh, 1H dan 13C NMR, dan spektroskopi masa. ================================================================================================ Isatins are precursors for synthesising organic compound, such as hydrazones. Hydrazones with azomentin groups have a bioactivity as antibacterial, anticancer, analgesic, antitumor, and anti-HIV. The research has been done successfully synthesized newly hydrazones are 2-thiophenecarbonylhydrazon-5-nitroisatin, 2-thiophenecarbonylhydrazon-5-methylisatin, 2- thiophenecarbonylhydrazon-(N-methyl)-5-nitroisatin, and 2- thiophenecarbonylhydrazon-(N-methyl)-5-methylisatin. The fourth hydrazones obtained 92%, 83%, 82%, and 58% yields respectively from reaction 5-methylisatin, 5-nitroisatin, N-methyl- 5-methylisatin and N-methyl-5-nitroisatin with 2- thiophenecarboxcylic acid hydrazide in ethanol as solvent with sulfuric acid as catalyst. N-methyl-5-methylisatin and N-methyl- 5-nitroisatin as reagents each obtained from reaction 5- methylisatin and 5-nitroisatin with sodium hydride and dimethyl sulfide in dimethyl sulfoxide as solvent in 88% and 76% yields. The identification of the results of synthesis by using NMR and mass spectroscopy.

Item Type: Thesis (Undergraduate)
Additional Information: RSKi 541.39 Fah s
Uncontrolled Keywords: Isatin, Hidrazona, Antibakteri
Subjects: Q Science > QD Chemistry > QD320 Cellulose. Hydrolysis
Divisions: Faculty of Mathematics and Science > Chemistry > 47201-(S1) Undergraduate Thesis
Depositing User: Yeni Anita Gonti
Date Deposited: 24 Feb 2020 06:36
Last Modified: 24 Feb 2020 06:36
URI: https://repository.its.ac.id/id/eprint/75139

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