Synthesis of 5,6-dimethoxyquinazolin-2(1H)-ones

Autor:	Elizabeth Wong, Jeffery B. Press, Jerry R. Roberts, David W. Graden, Ramesh M. Kanojia, James J. McNally, Robert A. Mallory, Zoltan G. Hajos, Edward G. Deegan, Bandurco Victor T, Mary Lou Cotter, John R. Lloyd
Rok vydání:	1986
Předmět:	chemistry.chemical_compound Liquid state chemistry Bicyclic molecule Stereochemistry Dimer Organic Chemistry Substituent Solid-state Nuclear magnetic resonance spectroscopy Carbon-13 NMR Combinatorial chemistry
Zdroj:	Journal of Heterocyclic Chemistry. 23:1821-1828
ISSN:	1943-5193 0022-152X
Popis:	Synthesis of 5,6-dimethoxyquinazolin-2(1H)-one derivatives was the subject of investigations leading to the preparation of title compounds 11, 13, 14 and 26. Target quinazolines 1 were synthesized in three ways; the route starting from o-vanillin via the intermediacy of 6-amino-2,3-dimethoxyacetophenone (19) was used for most of the preparative work. The unexpected formation of an acid-labile dimer of 13 was discovered and solid state 13C nmr was used for structural assignment. The 5-methoxy substituent in these systems shows anomalous spectral characteristics and, in one case, was cleaved in acid media to 22.
Databáze:	OpenAIRE
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