Tetrahedron

A new synthesis of 4-amino-2-quinolinones

J Bergman, A Brynolf, E Vuorinen

Index: Bergman, Jan; Brynolf, Anna; Vuorinen, Eino Tetrahedron, 1986 , vol. 42, # 13 p. 3689 - 3696

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Citation Number: 17

Abstract

Addition of Grignard or organolithium reagents to N-(α-haloacyl)-N-alkylsubstituted anthranilonitriles (eg N-(2-bromopropionyl)-N-methyl-2-cyanoaniline) induced anion formation followed by cyclization to 4-amino-2-quinolinones (eg 4-amino-1, 3-dimethyl-2- quinolinone (10)). Substrates lacking α-hydrogen atoms, such as N-(α-bromoisobutyryl)-2- cyanoaniline, also yielded 3, 3-diaethylquinolinedione (9b) by cyclization. In these cases ...