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Issue 5, 2003
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An alternative synthesis of 2-(N-arylhydrazono)-1-benzothiophen-3-ones

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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[double bond, length as m-dash]N double bond as evidenced by single crystal X-ray structure determination for 3b.

Graphical abstract: An alternative synthesis of 2-(N-arylhydrazono)-1-benzothiophen-3-ones

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Publication details

The article was received on 19 Nov 2002, accepted on 07 Jan 2003 and first published on 05 Feb 2003


Article type: Paper
DOI: 10.1039/B211458P
Org. Biomol. Chem., 2003,1, 822-825

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    An alternative synthesis of 2-(N-arylhydrazono)-1-benzothiophen-3-ones

    J. A. Zahra, B. A. Abu Thaher, M. M. El-Abadelah and R. Boese, Org. Biomol. Chem., 2003, 1, 822
    DOI: 10.1039/B211458P

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