Quinoline synthesis: scope and regiochemistry of photocyclisation of substituted benzylidenecyclopentanone O-alkyl and O-acetyloximes

M Austin, OJ Egan, R Tully, AC Pratt

Index: Austin, Mark; Egan, Oliver J.; Tully, Raymond; Pratt, Albert C. Organic and Biomolecular Chemistry, 2007 , vol. 5, # 23 p. 3778 - 3786

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Citation Number: 29

Abstract

Irradiation of substituted 2-benzylidenecyclopentanone O-alkyl and O-acetyloximes in methanol provides a convenient synthesis of alkyl, alkoxy, hydroxy, acetoxy, amino, dimethylamino and benzo substituted annulated quinolines. para-Substituents yield 6- substituted-2, 3-dihydro-1H-cyclopenta [b] quinolines with 8-substituted products being obtained from ortho-substituted starting materials. Reactions of meta-substituted ...