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Paper | Regular issue | Vol 51, No. 7, 1999, pp.1543-1561
Published online, 1st January, 1970
DOI: 10.3987/COM-99-8508
Synthesis of 3-Substituted 4-Hydroxyquinolin-2-ones via C-Acylation Reactions of Active Methylene Compounds with Functionalized 3,1-Benzoxazin-4-ones

Christos Mitsos, Alexandros Zografos, and Olga Igglessi-Markopoulou*

*Laboratory of Organic Chemistry, Department of Chemical Engineering, National Technical University of Athens, 9, Heroon Polytechniou St., Zografou Campus, 157 73 Athens, Greece

Abstract

A general protocol for the construction of 4-hydroxyquinolin-2-ones is described. Benzoxazinones react with the anion of active methylene compounds to produce the functionalized C-acylation compounds in very good yields. These key intermediates are cyclized to the desired quinolinones (25-40) under basic conditions. Spectral data and physical characteristics for all compounds are reported.