Annulation reactions with iron (III) chloride: oxidation of imines

…, D Nanni, A Tundo, G Zanardi, F Ruggieri

Index: Leardini, Rino; Nanni, Daniele; Tundo, Antonio; Zanardi, Giuseppe; Ruggieri, Fabrizio Journal of Organic Chemistry, 1992 , vol. 57, # 6 p. 1842 - 1848

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Citation Number: 54

Abstract

Aromatic imines react with phenylacetylene or styrene in an acetonitrile solution of iron (II1) chloride to give quinolines 3 or their tetrahydro derivatives 11 together with variable amounts of products 4 arising from the reduction of the imines. The initial step appears to be a one-electron oxidation to generate iron (I1) and an imine radical cation. When the reactions are carried out in the presence of stoichiometric amounts of tetrachloro- ...

~33%

~28%

~24%

~10%

~59%

~83%

~29%

~48%

~51%

Detail

~52%

~65%

~55%

~22%

~68%

Detail

~23%

Detail

~43%

~20%

~19%

~18%

Detail

~35%

~29%

~15%

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