Tetrahedron

α-Vinylation of β-aminothiophene derivatives. Synthesis of 6-functionalized thieno [3, 2-b] pyridines

M Berkaoui, F Outurquin, C Paulmier

Index: Berkaoui, M'hamed; Outurquin, Francis; Paulmier, Claude Tetrahedron, 1998 , vol. 54, # 31 p. 9055 - 9066

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Citation Number: 10

Abstract

The acid-catalyzed reductive α-alkylation of β-aminothiophenes was applied to the N-(thien- 3-yl) acetamide and alkyl N-(thien-3-yl) carbamates. Without reduction, β-amino α- vinylthiophenes were obtained when α-branched aldehydes were used. β-(3-Aminothien-2- yl) α, β-unsaturated ketones, esters and nitriles were also prepared from the corresponding α-functionalized acetals. These amines are intermediates in the formation of thieno [3, 2-b] ...