99933-56-9

Upstream product

• 92736-32-8 3-benzoyl-3,4-dihydro-4-quinazolinecarbonitrile 
• 99933-51-4 Benzoic acid cyano-(4-nitro-phenyl)-quinazolin-4-yl-methyl ester 
• 98512-28-8 Benzoic acid (4-nitro-phenyl)-quinazolin-4-yl-methyl ester 

Downstream Products

• 99933-61-6 4-(p-nitrophenyl)quinazoline 
• 62-23-7 4-nitro-benzoic acid 
• 99933-54-7 α-(p-nitrophenyl)-4-quinazolineacetonitrile 
• 36082-71-0 quinazoline-4-carbonitrile 

Relevant academic research and scientific papers

Reaction of 4-Aroylquinazolines with Sodium Hydroxide: Aryl Migration to Give 4-Aryl-3,4-dihydro-4-quinazolinecarboxylic Acids and Formation of Quinazoline and Aroic Acids

4-Aroylquinazolines (3) were prepared in good yields by alkaline hydrolysis of α-aryl-4-quinazolinylmethyl benzoates (15), followed by oxidation.The reaction of 3 with sodium hydroxide in dimethyl sulfoxide(DMSO) was found to proceed in two ways.One path is the aryl migration to lead to 4-aryl-3,4-dihydro-4-quinazolinecarboxylic acids (4), and the other is the fission of the C4-CO bond to yield quinazoline (5) and aroic acids (6). Potassium ferricyanide oxidized the carboxylic acids 4 to the corresponding 4-arylquinazolines (14) with elimination of carbon dioxide. Reaction of 4-benzoylquinazoline (3a) with methylmagnesium iodide did not result in the migration, but instead yielded of α-methyl-α-phenyl-4-quinazolinemethanol (18) and 3,4-dihydro-α,4-dimethyl-α-phenyl-4-quinazolinemethanol (19).