An alternative synthesis of 2-(N-arylhydrazono)-1-benzothiophen-3-ones |
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Authors: | Zahra Jalal A Abu Thaher Bassam A el-Abadelah Mustafa M Boese Roland |
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Institution: | Chemistry Department, Faculty of Science, University of Jordan, Amman-Jordan. |
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Abstract: | In the presence of triethylamine, 2-mercaptobenzoic acid readily adds onto acylhydrazonoyl chlorides (1a-c) (precursors of the reactive nitrile imine 1,3-dipolar species) to afford good yields of the corresponding 2-(2-oxo-1-arylhydrazonopropan-1-yl)mercapto]benzoic acids (2a-c). The latter acyclic adducts, in THF in the presence of 1,1'-carbonyldiimidazole, undergo intramolecular cyclization involving the activated carboxy and the enol functionality to deliver the respective 2-(N-arylhydrazono)-3-oxobenzothiophenes (3a-c). In the solid state, the latter compounds adopt the (Z)-geometry around the C=N double bond as evidenced by single crystal X-ray structure determination for 3b. |
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