First Synthesis of 3-Acetyl-2-aminothiophenes Using the Gewald Reaction

doi:10.3390/11050371

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Molecules 2006, 11(5), 371-376; doi:10.3390/11050371

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First Synthesis of 3-Acetyl-2-aminothiophenes Using the Gewald Reaction

Gernot A. Eller* and Wolfgang Holzer

Department of Drug Synthesis, Faculty of Life Sciences, University of Vienna, Austria

* Author to whom correspondence should be addressed.

Received: 5 May 2006; in revised form: 15 May 2006 / Accepted: 16 May 2006 / Published: 16 May 2006

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Abstract: Novel 3-acetyl-2-aminothiophenes were prepared from cyanoacetone and1,4-dithianyl-2,5-diols using a modified Gewald reaction. The syntheses of thecorresponding acetamides, as well as that of 3-acetyl-2-amino-5-nitrothiophene – aninteresting building-block for thiophene azo dyes – are reported. Detailed spectroscopicinvestigations (¹H-NMR, ¹³C-NMR, MS, IR) of the obtained compounds are presented.

Keywords: Gewald reaction; Thiophene synthesis; Cyclization; Condensation.

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MDPI and ACS Style

Eller, G.A.; Holzer, W. First Synthesis of 3-Acetyl-2-aminothiophenes Using the Gewald Reaction. Molecules 2006, 11, 371-376.

AMA Style

Eller GA, Holzer W. First Synthesis of 3-Acetyl-2-aminothiophenes Using the Gewald Reaction. Molecules. 2006; 11(5):371-376.

Chicago/Turabian Style

Eller, Gernot A.; Holzer, Wolfgang. 2006. "First Synthesis of 3-Acetyl-2-aminothiophenes Using the Gewald Reaction." Molecules 11, no. 5: 371-376.

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