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Paper | Regular issue | Vol 32, No. 11, 1991, pp.2151-2159
Published online, 1st January, 1970
DOI: 10.3987/COM-91-5823
Synthesis and Tautomerism of 2,4-Dihydroxyquinolines

José Luis García Ruano,* Concepción Pedregal, and Jesús H. Rodrìguez*

*Departamento de Química Orgánica, Facultad de Ciencias, Universidad Autónoma de Madrid, Cantoblanco, 28049-Madrid, Spain

Abstract

The reaction of ethyl N-[2-(2-Z-acetyl)phenylcarbamates with NaH/THF yields 3-Z-2,4-dihydroxyquinolines [Z=SMe, SOMe, SO2Me and CN]. The study of the tautomeric equilibria of all these substrates by 13C-nmr shows that thioether and nitrile exhibit the 2-quinolone structure, whereas the sulfoxide and probably the sulfone exist as 4-quinolone tautomers.