0000000000073862
AUTHOR
Alexandra Romek
Microwave-Assisted Synthesis of Polysubstituted 4-Quinolones from Deprotonated α-Aminonitriles
The α-alkylation of deprotonated N-aryl-α-aminonitriles with α-bromoesters furnishes intermediates that can be cyclized to 4-quinolones upon microwave irradiation. Alternatively, base-induced dehydrocyanation of the alkylation products furnishes enaminoesters, which can, for example, be converted into quinoline-3-carboxylates.
ChemInform Abstract: Microwave-Assisted Synthesis of Polysubstituted 4-Quinolones from Deprotonated α-Aminonitriles.
The α-alkylations of deprotonated Strecker products such as (I) or (V) give a series of intermediates such as (III), (VI), or (X), which undergo microwave-assisted HCN and EtOH eliminations leading to the title quinolones (IV), (VII)/(VIII), or (XI).