| Diverse Synthesis of Substituted Pyrazolo Benzothiazole Compounds through Novel Transformations of 2-Benzothiazolyl Acetohydrazide derivatives |
| Paper ID : 1016-ISCHU |
| Authors |
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Heba abdelazeem elboshi *, Rasha Abdullah Azzam, Galal El-Din H Elgemeie Chemistry Department, Faculty of Science, Helwan University, Egypt |
| Abstract |
| Benzothiazole derivatives, with diverse biological and medicinal attributes, have gained attention. Benzothiazole is an essential bicyclic structure present in natural products. A literature search explored their synthesis, anti-tumor, anti-inflammatory, anti-convulsant, antioxidant, and antimicrobial properties. Several methodologies have been accomplished to synthesize benzothiazole compounds. In this work, an unpredicted transformation of 2-benzothiazolyl acetohydrazide to yield 4-(1,3-benzothiazol-2-yl)-1,2-dimethyl-1,2-dihydro-3H-pyrazol-3-one compounds has been formed under ambient conditions upon treatment with N,N-dimethylformamide dimethyl acetal (DMF-DMA). The resulting structure's authenticity was validated through X-ray crystallography. Further unanticipated transmutation was witnessed during the reaction between N-(2-(benzo[d]thiazole-2-yl)acetyl)benzensulfonohydrazide and DMF-DMA in ethanol as solvent. This process facilitated the production of 4-(1,3-benzothiazol-2-yl)-1,2-dihydro-3H-pyrazol-3-one through intramolecular cyclization, accompanied by the removal of the sulfonyl moiety. Analogous conversion was observed as N-(2-(benzo[d]thiazole-2-yl)acetyl)benzensulfonohydrazide was subjected to sequential treatment with carbon disulfide under ethanolic sodium ethoxide conditions, succeeded by reaction of the resultant product with methyl iodide. This latter sequence concluded in the formation of 4-(benzo[d]thiazol-2-yl)-5-(methylthio)-1H-pyrazol-3(2H)-one in good yield. The structure of the resulting compounds was confirmed through the utilization of spectral and elemental analysis techniques. |
| Keywords |
| Benzothiazole Compounds, Pyrazolo Benzothiazole Compounds and 2-Benzothiazolyl Acetohydrazide derivatives |
| Status: Abstract Accepted (Poster Presentation) |