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A new synthesis of 4-amino-2-quinolinones

✍ Scribed by Jan Bergman; Anna Brynolf; Eino Vuorinen


Publisher
Elsevier Science
Year
1986
Tongue
French
Weight
603 KB
Volume
42
Category
Article
ISSN
0040-4020

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✦ Synopsis


Addition of Crignard or organolithium reagents to R-(a-haloacyl)-g-alkylsubstituted anthranilonitriles (e.g. B-(2-bromopropionyl)-N-methyl-2-cyanoaniline) induced anion formation followed by cyclization to I-amino-2quinolinones (e.g. I-amino-1,3-dimethyl-2-quinolinone (1Q)). Substrates lacking a-hydrogen atoms, such as p-(a-bromoisobutyryl)-2_cyanoaniline, also yielded 3,3-dimethylquinolinedione (B) by cyclization.

In these cases the initial step is a halogen-metal exchange reaction.


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