The use of benzenesulfonyl substituted furoxans as flexible intermediates for the synthesis of new functionalized furoxans interesting for their potential biological properties is discussed. Reaction of benzenesul-fonylphenylsulfonylfuroxan isomers 7a and 7b with ethanol and ethanethiol in basic medium affords the expected ethers and sulphides respectively. Reaction of bis(benzenesulfonyl)furoxan (1) with ethanol in basic medium gives 3-benzenesulfonyl-4-ethoxyfuroxan (2) or diethoxyfuroxan (3), according to the experimental procedure. In contrast the reaction of 1 with ethanethiol gives a mixture of substitution compounds and the 4-benzenesulfonyl-3-ethylthiofurazan (11). The structure of the compounds has been assigned by nmr spectroscopy and, in the case of 3-benzenesulfonyl-4-ethylthiofuroxan (9b), confirmed by X-ray analysis.

Unsymmetrically substituted furoxans. Part 16 [1]. Reaction of benzenesulfonyl substituted furoxans with ethanol and ethanethiol in basic medium

SORBA, Giovanni;ERMONDI, Giuseppe;FRUTTERO, Roberta;GALLI, Ubaldina;GASCO, Alberto
1996

Abstract

The use of benzenesulfonyl substituted furoxans as flexible intermediates for the synthesis of new functionalized furoxans interesting for their potential biological properties is discussed. Reaction of benzenesul-fonylphenylsulfonylfuroxan isomers 7a and 7b with ethanol and ethanethiol in basic medium affords the expected ethers and sulphides respectively. Reaction of bis(benzenesulfonyl)furoxan (1) with ethanol in basic medium gives 3-benzenesulfonyl-4-ethoxyfuroxan (2) or diethoxyfuroxan (3), according to the experimental procedure. In contrast the reaction of 1 with ethanethiol gives a mixture of substitution compounds and the 4-benzenesulfonyl-3-ethylthiofurazan (11). The structure of the compounds has been assigned by nmr spectroscopy and, in the case of 3-benzenesulfonyl-4-ethylthiofuroxan (9b), confirmed by X-ray analysis.
33
327
334
G. Sorba; G. Ermondi; R. Fruttero; U. Galli; A. Gasco
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2318/69244
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