58045-62-8

Upstream product

• 1885-29-6 anthranilic acid nitrile 
• 491-36-1 4-quinazolinol 
• 5190-68-1 4-chloroquinazoline 
• 13331-27-6 m-nitrobenzene boronic acid 
• 99933-52-5 Benzoic acid cyano-(3-nitro-phenyl)-quinazolin-4-yl-methyl ester 
• 1227920-69-5 (E)-N’-(2-cyanophenyl)-N,N-dimethylformimidamide 

Downstream Products

• 1258282-49-3 3-(quinazolin-4-yl)aniline 

Relevant academic research and scientific papers

“On-Water” Palladium-Catalyzed Tandem Cyclization Reaction for the Synthesis of Biologically Relevant 4-Arylquinazolines

The quinazoline scaffold is prevalent in pharmaceutically relevant molecules that show diverse biological activities. Herein, we report an efficient “on-water” palladium-catalyzed tandem cyclization reaction from commercially available arylboronic acids and benzonitriles that enable the rapid access to 4-arylquinazoline scaffolds in good to excellent yields (45 examples, up to 98 % yield). This protocol has shown good functional group tolerance and broad substrate scope. The reaction was also performed on a gram scale and successfully applied to the synthesis of the highly potent and selective PI3Kδ inhibitor N11, showing the practicability and synthetic utility of the protocol. In this reaction, the quinazoline scaffold is efficiently constructed with the simultaneous formation of one C?C bond and one C?N bond. Collectively, the protocol could serve as an alternative strategy to synthesize biologically important quinazoline scaffolds.

4-arylquinazoline compounds and preparation method thereof

The invention provides 4-arylquinazoline compounds which have a general formula as shown in the specification, wherein R represents hydrogen, halogen, alkane, nitro or alkoxy, R represents hydrogen or methyl, Ar represents groups as shown in the specification, and R represents hydrogen, halogen, alkane, alkoxy, nitro, hydroxy, trifluoromethyl, phenyl or methoxycarbonyl; the compounds enrich the structures of 4-arylquinazoline compounds, and provide a material basis for further study on the potential biological activity of the compounds. The invention also provides a preparation methodof the compounds, which comprises the following step: cyanophenyl raw materials react with aromatic phenylboronic acid ArB(OH)2 in a sealed environment under the action of a palladium salt catalyst,a bidentate chelating ligand, a Lewis acid and a solvent at 30-300 DEG C to form the 4-arylquinazoline compounds; a structural formula of the 4-arylquinazoline compounds is shown in the specification,and the preparation method provided by the invention has the advantages of no need of inert gas protection, mild reaction conditions, short reaction time, high yield and the like.

CYCLIC SULFONAMIDE CONTAINING DERIVATIVES AS INHIBITORS OF HEDGEHOG SIGNALING PATHWAY

The invention relates generally to the creation and use of cyclic sulfonamide containing derivatives to inhibit the hedgehog signaling pathway and to the use of those compounds for the treatment of hyperproliferative diseases and angiogenesis mediated diseases.

ISOQUINOLINE, QUINOLINE, AND QUINAZOLINE DERIVATIVES AS INHIBITORS OF HEDGEHOG SIGNALING

The invention provides isoquinoline, quinoline, and quinazoline derivatives to treat a variety of disorders, diseases and pathologic conditions, and more specifically to the use of isoquinoline, quinoline, and quinazoline derivatives to inhibit the hedgehog signaling pathway and to the use of those compounds to the treatment of hyperproliferative diseases and pathologic angiogenesis.

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).