Iodine-mediated intramolecular electrophilic aromatic cyclization in allylamines: A general route to synthesis of quinolines, pyrazolo[4,3-b] pyridines, and thieno[3,2-b]pyridines
An unprecedented synthesis of aromatic ring annulated pyridines from suitably substituted primary allylamines via intramolecular electrophilic aromatic cyclization mediated by molecular iodine under mild conditions is described.
α-vinylation of β-aminothiophene derivatives. Synthesis of 6- functionalized thieno[3,2-b]pyridines
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.
Berkaoui, M'hamed,Outurquin, Francis,Paulmier, Claude
p. 9055 - 9066
(2007/10/03)
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