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. 2006 May 16;11(5):371-6.
doi: 10.3390/11050371.

First synthesis of 3-acetyl-2-aminothiophenes using the Gewald reaction

Gernot A Eller  1 , Wolfgang Holzer
Affiliations

First synthesis of 3-acetyl-2-aminothiophenes using the Gewald reaction

Gernot A Eller et al. Molecules. .

Abstract

Novel 3-acetyl-2-aminothiophenes were prepared from cyanoacetone and 1,4-dithianyl-2,5-diols using a modified Gewald reaction. The syntheses of the corresponding acetamides, as well as that of 3-acetyl-2-amino-5-nitrothiophene - an interesting building-block for thiophene azo dyes - are reported. Detailed spectroscopic investigations ((1)H-NMR, (13)C-NMR, MS, IR) of the obtained compounds are presented.

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Figures

Scheme 1
Scheme 1
The classical Gewald thiophene synthesis.
Scheme 2
Scheme 2
Synthesis of the title compounds 4 and the corresponding acetamides 5.
Scheme 3
Scheme 3
Preparation of the thiophene azo-dye building block 7.
See this image and copyright information in PMC

References

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