91859-59-5

Upstream product

• 3337-86-8 quinazoline-4-thiol 
• 4870-65-9 2-bromophenylacetic acid 
• 95616-37-8 S-(4-quinazolinyl)-α-phenylthioglycolic acid 
• 3337-86-8 quinazoline-4(3H)-thione 
• 82323-46-4 phenylglyoxylic acid chloride p-toluenesulfonylhydrazone 
• 41036-93-5 2‐bromo‐2‐chloro‐1‐phenylethan‐1‐one 
• 19078-72-9 bromo(phenyl)acetyl chloride 

Downstream Products

• 95616-55-0 C₂₂H₁₇N₃O₃S 
• 95616-54-9 11-Acetyl-9-phenyl-pyrido[1,2-c]quinazolin-8-one 
• 95616-62-9 3-Phenyl-pyrrolo[1,2-c]quinazoline-1-carboxylic acid 
• 95616-63-0 3-phenylpyrrolo<1,2-c>quinazoline 
• 95616-53-8 8-Oxo-9-phenyl-8H-pyrido[1,2-c]quinazoline-10,11-dicarbonitrile 
• 91534-02-0 3-Phenyl-2,3-dihydro-pyrrolo[1,2-c]quinazoline-1,2-dicarboxylic acid dimethyl ester 
• 91534-01-9 C₂₂H₁₈N₂O₅S 
• 91534-00-8 C₂₁H₁₈N₂O₃S 
• 91533-97-0 3-Phenyl-2,3-dihydro-pyrrolo[1,2-c]quinazoline-1-carboxylic acid ethyl ester 
• 91534-03-1 8-Oxo-9-phenyl-8H-pyrido[1,2-c]quinazoline-10,11-dicarboxylic acid dimethyl ester 
• 95616-43-6 [2-(4-Hydroxy-5-phenyl-thiazol-2-yl)-phenyl]-carbamic acid 
• 95616-56-1 C₂₆H₁₇N₃O₃S 
• 91533-98-1 ethyl 3-phenylpyrrolo<1,2-c>quinazoline-1-carboxylate 

Relevant academic research and scientific papers

MESOIONIC COMPOUNDS WITH A BRIDGED NITROGEN ATOM. 17. THIAZOLOQUINAZOLINIUM 3-OXIDES

The cyclization of (4-quinazolinylthio)phenylacetic and acetic acids gives extremely reactive thiazoloquinazolinium 3-oxides, which, depending on the structure of the mesoionic ring, react with either electrophilic or nucleophilic reagents.

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.

Carbenoid Intermediates in the Synthesis of Mesoionic Anhydro-4-hydroxythiazolium Hydroxides

α-(Tosylhydrazono)phenylacetyl chloride and N-monosubstituted thioamides in dry, non-protic solvents and in the presence of Et3N give representatives of the title mesoionic ring system in good to excellent yields; carbene or carbenoid type intermediates a

Cycloaddition of Anhydro-3-hydroxy-2-phenylthiazoloquinazolin-4-ium Hydroxide with Olefinic Dipolarophiles

Anhydro-3-hydroxy-2-phenylthiazoloquinazolin-4-ium hydroxide (1) underwent cycloaddition with ethyl acrylate and dimethyl fumarate to give pyrroloquinazoline derivatives and COS, whereas with acetylenic dipolarophiles the anticipated