107288-91-5

Upstream product

• 60751-76-0 N-propionyl-anthranilonitrile 
• 109271-69-4 1-benzoyl-2-ethyl-1,2-dihydro-4-phenylquinazoline-2-carbonitrile 
• 622-76-4 1-phenyl-1-butyne 
• 5439-98-5 2-phenyl-2,3-dihydro-phthalazine-1,4-dione 
• 2835-77-0 (2-aminophenyl)(phenyl)methanone 
• 115-80-0 Triethyl orthopropionate 
• 109271-56-9 1-benzoyl-1,2-dihydro-4-phenylquinazoline-2-carbonitrile 
• 17629-01-5 4-phenylquinazoline 
• 549500-24-5 N-(2-benzoylphenyl)propionamide 

Relevant academic research and scientific papers

Preparation of 4-arylquinazolines with: O-(N-alkyl, N-p-tosyl)aminobenzonitriles, aryllithiums, and NIS

The treatment of o-(N-alkyl,N-p-tosyl)aminobenzonitriles with aryllithiums, followed by the reaction with water, NIS under irradiation with a fluorescent lamp, and then tBuOK gave 2-alkyl-4-arylquinazolines or 4-arylquinazolines in good to moderate yields. The present reaction proceeds through the formation of N-iodoimines from imines with NIS, the generation of iminyl radicals, the 1,6-H shift by iminyl radicals, the cyclization via 6-exo-tet mode, and finally the elimination of p-toluenesulfinate to generate 2-alkyl-4-arylquinazolines or 4-arylquinazolines.

Ru(II)-Catalyzed C-H Activation and Annulation Reaction via Carbon-Carbon Triple Bond Cleavage

An unprecedented Ru(II)-catalyzed C-H activation and annulation reaction, which proceeds via C-C triple bond cleavage, is reported. This reaction of 2-phenyldihydrophthalazinediones with alkynes, which works most efficiently in the presence of bidented ligand 1,3-bis(diphenylphosphino)propane, affords good yields of substituted quinazolines.

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.

STUDIES WITH REISSERT COMPOUNDS. PART 17. MONO-REISSERT COMPOUND FORMATION AT THE 1,2-POSITION OF THE QUINAZOLINE SYSTEM.

4-Substituted quinazolines have been selectively converted into mono-Reissert compounds at the 1,2-position by use of acid chlorides and trimethylsilyl cyanide.Various reactions of the quinazoline Reissert compounds are reported.For example, conjugate base generation at the 2-position leads to a 1,2-rearrangement, whereas substitution occurs in the presence of an alkyl halide, providing, after hydrolysis, 2-alkyl-4-phenylquinazolines in good yield.Ring annellation by intramolecular alkylation is also reported.The quinazoline Reissert compound conjugate base reacts with aldehydes to give alcohol esters which can further be converted, via the alcohol and use of phosgene, to novel oxazoloquinazoline derivatives.

SYNTHESIS OF QUINAZOLINES

Grignard reagents reacted with 2-aminobenzonitrile to give the intermediate (10), which readily could be cyclized to quinazolines by reaction with carbonyl compounds (e.g. acid chlorides, anhydrides, formates and oxalates).The intermediate (10) and aldehy