SYNTHESIS AND CHARACTERIZATION OF TWO NOVEL THIOFIBRATES DERIVED FROM 7-HYDROXY-4-METHYL-2H CHROMEN-2-ONE
| Main Author: | Niranjan M.S. * and Chaluvaraju K.C |
|---|---|
| Format: | Article Journal |
| Terbitan: |
, 2018
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| Subjects: | |
| Online Access: |
https://zenodo.org/record/1345716 |
Daftar Isi:
- ABSTRACT Two novel thiofibrates bearing 1,3,4-oxadizole and 1,2,4-triazole are prepared from 7-hydroxy-4-methyl-2H-chromen-2-one (1). The compound (1) is obtained by treating resorcinol with ethyl acetate in the presence of concentrated sulphuric acid. It is then treated with ethylchloroacetate to get ethyl((4-methyl-2-oxo-2H-chromen-7-yl)oxy)acetate (2). This on hydrogenolysis gives 2-((4-methyl-2-oxo-2H-chromen-7-yl)oxy)acetohydrazide (3) which on further reaction with phenyl isothiocyanate in presence of sodium hydroxide gives4-methyl-7-((5-sulfanyl-4H-1,2,4-triazol-3-yl)methoxy)-2H-chromen-2-one (4). Also the compound (3) on reaction with carbon disulphide in presence of powdered 10% potassium hydroxide gives 4-methyl-7-((5-sulfanyl-1,3,4-oxadiazol-2-yl)methoxy)-2H-chromen-2-one (5). The compounds (4) and (5) on reaction with ethyl-2-bromo isobutyrate in presence of anhydrous potassium carbonate in DMF forms ethyl 2-methyl-2-((5-{((4-methyl-2-oxo-2H-chromen-7-yl)oxy)methyl}-4H-1,2,4-triazol-3-yl)sulfanyl)propanoate (6) and ethyl-2-methyl-2-((5-{((4-methyl-2-oxo-2H-chromen-7-yl)oxy)methyl}-1,3,4-oxadiazol-2-yl)sulfanyl)propanoate (7) respectively. The reaction progress was monitored by TLC. The structures of the synthezised compounds were characterized by physical data-m.p, Rf. and spectral investigations of IR and 1H NMR. KEYWORDS: 7-hydroxy-4-methyl coumarin, 1,3,4-oxadizole, 1,2,4-triazole, ethyl-2-bromo isobutyrate, DMF, ethyl-2-bromo-isobytatrate.