Novel thiophene derivatives and methods for producing the same

Details Novel thiophene derivatives and methods for producing the same Novel thiophene derivatives and methods for producing the same

1990-08-20

1992-03-31

Siegel, Alan

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

549 70, C07D33338, C07D33322

Patent

active

051010496

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)ethylithiophenes are obtained either by 0-alkylation of 2-acetylthiophene oxime or by directly reacting 2-acetylthiophene with an 0-alkylhydroxylamine.

REFERENCES:
patent: 2636883 (1953-04-01), Byrns
patent: 3658850 (1972-04-01), Davies

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