4015-28-5

Usage

Uses

Used in Pharmaceutical Industry:
6-Chloro-4-phenylquinazoline is used as a key intermediate in the synthesis of 6-chloro1,4-dihydro-1-methyl-4-phenyl-4-quinazolinol (C371025), a compound with potential therapeutic applications. Its role in the pharmaceutical industry is to facilitate the development of new drugs by providing a building block for the creation of more complex molecules with specific biological activities.

Upstream product

• 136440-59-0 (Z)-2-Amino-5-chlorbenzophenonamidinohydrazon-acetat 
• 136440-60-3 (E)-2-Amino-5-chlorbenzophenonamidinohydrazon-acetat 
• 5958-08-7 6-chloro-4-phenylquinazoline-2-carboxylic acid 
• 153681-82-4 6-chloro-1,2-dihydro-4-phenylquinazoline-2-carboxylic acid 
• 27610-14-6 3-amino-6-chloro-3,4-dihydro-4-hydroxy-4-phenylquinazoline 
• 4016-85-7 5-chloro-2-(chloroacetylamino)benzophenone 
• 719-59-5 5-chloro-2-aminobenzophenone 
• 88190-77-6 6-chloro-3,4-dihydro-4-phenylquinazoline-2-carboxylic acid 
• 50-00-0 formaldehyd 
• 6628-86-0 5-chloro-2-nitrobenzaldehyde 
• 20028-53-9 2-amino-5-chlorobenzaldehyde 
• 516-06-3 D,L-valine 
• 2835-06-5 phenylglycin 
• 56-40-6 glycine 

Downstream Products

• 13132-91-7 1-(6-chloro-4-phenylquinazolin-2-yl)ethan-1-one 

Relevant academic research and scientific papers

Palladium(II)-Catalyzed Three-Component Tandem Cyclization Reaction for the One-Pot Assembly of 4-Arylquinazolines

A one-pot method for joining three separate components leading to an assortment of 4-arylquinazolines (27 examples) in good to excellent yields is described. The method consists of a palladium(II)-catalyzed?-cascade reaction involving C(sp)-C(sp 2/s

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.

“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.

Copper-catalyzed oxidative amination of methanol to access quinazolines

A novel method for the copper-catalyzed oxidative amination of 2′-aminoarylketones with methanol as a C1 carbon source and ammonium acetate as an amine source to construct quinazolines was established in a one-pot manner. The reaction conditions are straightforward and highly atom economic to deliver the corresponding quinazolines in high yields with wide functional group tolerance. Importantly, the present method is applicable on a multigram scale and its synthetic utility is demonstrated by synthesizing quazodine, a muscle-relaxing drug in high yields.

Silver-Catalyzed Isocyanide Insertion into N?H Bond of Ammonia: [5+1] Annulation to Quinazoline Derivatives

A silver-catalyzed [5+1] annulation of o-acylaryl isocyanides with ammonium acetate and hydroxlamine was developed for the efficient and practical synthesis of quinazolines and quinazoline 3-oxides in good to excellent yields, respectively. The domino process involved an unprecedented isocyanide insertion into the N?H bond of ammonia or hydroxylamine and followed by condensation reaction at ambient conditions. (Figure presented.).

TBHP as Methyl Source under Metal-Free Aerobic Conditions To Synthesize Quinazolin-4(3H)-ones and Quinazolines by Oxidative Amination of C(sp3)–H Bond

tert-Butyl hydroperoxide (TBHP) served as the methyl source under metal-free aerobic conditions in the oxidative amination of the C(sp3)–H bond to synthesize quinazolin-4(3H)-ones and quinazolines from 2-aminobenzamides and 2-carbonyl-substituted anilines, respectively.

One-pot three-component synthesis of quinazolines: Via a copper-catalysed oxidative amination reaction

A copper-catalysed three-component reaction for constructing a series of quinazoline derivatives has been developed. In this system, solvents act as the reactants and different functional groups are well tolerated to obtain corresponding products in moderate to good yields.

I2-catalyzed aerobic oxidative C(sp3)-H amination/C-N cleavage of tertiary amine: Synthesis of quinazolines and quinazolinones

An iodine-catalyzed oxidative C(sp3)-H amination/C-N cleavage of tertiary amines couducted under an oxygen atmosphere has been developed and affords a route to quinazolines and quinazolinones in good to excellent yields via a domino ring annulation. The method is metal-free, peroxide-free, and operationally simple to implement with a wide scope of substrates and represents a new avenue for multiple C-N bond formations.

Asymmetric hydrogenation of quinazolinium salts catalysed by halide-bridged dinuclear iridium complexes bearing chiral diphosphine ligands

Asymmetric hydrogenation of quinazolinium salts was catalysed by halogen-bridged dinuclear iridium complexes bearing chiral diphosphine ligands, yielding tetrahydroquinazoline and 3,4-dihydroquinazoline with high enantioselectivity. A derivative of chiral dihydroquinazoline was used as a chiral NHC ligand. This journal is

An Efficient Three-component, One-pot Synthesis of Quinazolines under Solvent-free and Catalyst-free Condition

An efficient green protocol for the synthesis of quinazolines in the absence of solvent and catalyst has been developed. 2,4-Disubstituted quinazolines have been synthesized from three-component one-pot reactions of 2-aminoaryl ketones, orthoesters, and ammonium acetate. The present method has advantages of operational simplicity, substrate generality, clean reaction, high yields (76-94%), and moderate reaction time. The plausible mechanism of the reaction has been proposed based on the spectral characterization and single crystal X-ray analysis of isolated intermediate.