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.
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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: | http://repository.its.ac.id/id/eprint/75139 |
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