Tetrahedron p. 9055 - 9066 (1998)
Update date:2022-08-05
Topics:
Berkaoui, M'hamed
Outurquin, Francis
Paulmier, Claude
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]pyridines bearing a functional group at the β-position of the pyridine ring.
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