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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 9, 1979 - Issue 8
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Original Articles

A Convenient Synthesis of 2-Substituted 3-Hydroxy- and 3-Amino-Thiophens from Derivatives of 2-Chloroacrylic Acid

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Pages 731-734 | Received 04 May 1979, Published online: 05 Dec 2006
 

Abstract

A valuable synthesis of methyl 3-amino-1 and 3-hydroxy-2 2-thiophen carboxylates, due to Fiesselmann, involves the base-induced condensation of methyl thioglycollate with 2,3-dihalogeno-propionitrile and 2,3-dihalogenopropionate esters, respectively. It seemed to us that readily accessible 2-halogenoacrylic acid derivatives might be useful substitutes for the halogenated compounds previously employed in these reactions. Accordingly we have used compounds (1a) and (1b) in a modification of the Fiesselmann process, and have obtained good yields of the thiophen derivatives (2a) and (2b):-

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