INVESTIGADORES
ORELLI Liliana Raquel
artículos
Título:
Chemical properties of pyrimidoquinoxaline 6-oxides
Autor/es:
MARÍA BEATRIZ GARCÍA; LILIANA R. ORELLI; ISABEL A. PERILLO
Revista:
JOURNAL OF HETEROCYCLIC CHEMISTRY
Editorial:
HeteroCorporation
Referencias:
Lugar: USA; Año: 2006 vol. 43 p. 1703 - 1707
ISSN:
0022-152X
Resumen:
The reactivity of some representative 5-arylpyrimidoquinoxaline 6-oxides 1 was investigated. Reduction with sodium borohydride afforded the corresponding N-deoxy compounds 2. Reaction with methyl iodide in excess led selectively to N-methyl derivatives 3. The preference for N vs. O-alkylation is analyzed considering electronic effects. Alkaline hydrolysis of compounds 1 involved initial nucleophilic attack to the amidine carbon (C4a), and subsequent regioselective ring opening leading to 4-(3-aminopropyl)-2-aryl-quinoxaline-3-one 1-oxides 4. The regioselectivity observed in alkaline hydrolysis is also discussed.
