1,2-Dihydro-4-quinazolinones from anthranilic amides and oxo-compounds - Studies of the ring closure using MNDO calculations
Heating of anthranilic amides 1a-c with oxo-compounds without solvent represents a simple synthetic access to 1,2-dihydro-4-quinazolinones 8-25. Under drastic conditions β-dicarbonyl compounds give the methylquinazolinones 26/27 by elimination. Thermodynamic control explicates the course of the reactions and the formation of the products. The enaminones 28/29 isolated from cyclic β-diketones are transformed to quinazolinyl pentanones 34/35 in the presence of acetic acid. The ring transformation is explained by perturbation theory.
Lessel
p. 571 - 579
(2007/10/02)
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