Thiophene derivatives and methods for producing the same
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United States of America Patent
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Dec 20, 1988
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N/A
app pub date -
Mar 21, 1988
filing date -
May 13, 1986
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Abstract
Novel compounds, 2-(.alpha.-alkoxyimino)ethylthiophenes are susceptible to electrophilic substitution reactions, and the acetylation, nitration, sulfonation and halogenation of the compounds provide 5-acetyl-2-(.alpha.-alkoxyimino)ethylthiophenes, 5-nitro-2-(.alpha.-alkoxyimino)ethylthiophenes, 5-(.alpha.-alkoxyimino)ethyl-2-thiophenesulfonic acid and 5-halo-2-(.alpha.-alkoxyimino)ethylthiophenes, respectively. The hydrolysis of 5-acetyl-2-(.alpha.-alkoxyimino)ethylthiophenes readily provides a known compound, 2,5-diacetylthiophene which is an important intermediate for the production of medicines, whereas the haloform reaction provides novel compounds, 5-(.alpha.-alkoxyimino)ethyl-2-thiophenecarboxylic acids, the hydrolysis of which compounds readily provides a known compound, 5-acetyl-2-thiophenecarboxylic acids, an important intermediate for the production of medicines. The hydrolysis of 5-(.alpha.-alkoxyimino)ethyl-2-thiophenesulfonic acids and their salts provide novel 5-acetyl-2-thiophenesulfonic acid and its salts, respectively. Novel compounds, 2-(.alpha.-alkoxyimino)ethylthiophenes are obtained either by 0-alkylation of 2-acetylthiophene oxime or by directly reacting 2-acetylthiophene with an 0-alkylhydroxylamine.
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