74374-97-3Relevant academic research and scientific papers
Bis-azaheterocycles: Part IV - Thermal and photochemical reactions of some 3,3'-bisquinazoline-4,4'-diones
Reddy, P. S. N.,Bhavani, A. K. D.
, p. 683 - 685 (2007/10/02)
Pyrolysis of 2,2'-di(2-chlorophenyl)-3,3'-bis(1,2,3,4-tetrahydroquinazoline)-4,4'-dione (1) at 270 deg C gives 2-(2-chlorophenyl)-1,2-dihydro-4(3H)-quinazolinone (4) and 2-(2-chlorophenyl)-4(3H)-quinazolinone (5).Similarly the pyrolysis of 2,2'-diaryl-1,1'-dimethyl-3,3'-bis(1,2,3,4-tetrahydroquinazoline)-4,4'-dione (2a, Ar=phenyl, 2b, Ar=4-methoxyphenyl) yields 2-aryl-1-methyl-1,2-dihydro-4-(3H)-quinazolinone (6a/6b) and 2-aryl-1-methyl-4-(3H)-quinazolinone (7a/7b) along with a dimeric compound 3,3'-diaryl-1,1'-dimethyl-2,2'-bis(1,2,3,4-tetrahydroquinazoline)-4,4'-dione (8a/8b).However, thermolysis of 3,3'-bis(spiro-4'(3'H)-one) (3) at 275 deg C affords 2,5-di(2-aminophenyl)-1,3,4-oxadiazole (9) and 1,2,3,4-tetrahydro-9(10H)acridinone (10).Photolysis of 1, 2a, 2b and 3 furnishes the products 5, 7a, 7b and spiro-4'(3'H)-one (11) respectively.
1,2-Dihydro-4-quinazolinones from anthranilic amides and oxo-compounds - Studies of the ring closure using MNDO calculations
Lessel
, p. 571 - 579 (2007/10/02)
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.
