91533-99-2

Upstream product

• 16347-74-3 ethyl α-phenyl(4-oxoquinazolin-3-yl)acetate 
• 491-36-1 4-Hydroxyquinazoline 
• 2882-19-1 ethyl 2-phenyl-2-bromoacetate 

Downstream Products

• 95616-62-9 3-Phenyl-pyrrolo[1,2-c]quinazoline-1-carboxylic acid 
• 95616-63-0 3-phenylpyrrolo<1,2-c>quinazoline 
• 91533-98-1 ethyl 3-phenylpyrrolo<1,2-c>quinazoline-1-carboxylate 

Relevant academic research and scientific papers

Annulation of the Quinazoline Ring Utilizing Mesoionic Ring Systems

anhydro-3-Hydroxythiazoloquinazolin-4-ium hydroxides, prepared from the corresponding thioglycolic acid with cyclodehydrating agents and also from 4(3H)-quinazolinethiones and α-bromophenylacetyl chloride, were hydrolyzed at the 5-position of the quinazoline ring with hot water.Alkynic and alkenic dipolarophiles cycloadded readily in hot benzene; the former gave pyridoquinazolines and the latter 1:1 cycloadducts which lost H2S to give the above ring system.These procedures provided convenient annulation of a pyridinone to the c side of quinazoline.With ethyl acrylate, in addition to the normal 1:1 cycloadduct, a rearranged pyrroloquinazoline was obtained depending on the reaction conditions; analogous products were obtained with dimethyl fumarate. anhydro-1-Hydroxythiazoloquinazolinium hydroxides, preferably generated in situ from the corresponding thioglycolic acid and dicyclohexylcarbodiimide (DCC), and alkynic dipolarophiles in refluxing benzene readily gave pyridoquinazolines.Alkenic dipolarophiles also gave 1:1 cycloadducts, which lost H2S to form pyridoquinazolines, resulting in annulation of a pyridinone ring to the a side of quinazoline.