3440-47-9

Upstream product

• 700-79-8 2-methylquinazoline 
• 14371-10-9 (E)-3-phenylpropenal 
• 4403-69-4 2-amino-1-benzylamine 
• 758640-21-0 N-Benzylaniline 
• 104-55-2 3-phenyl-propenal 
• 104-54-1 3-Phenylpropenol 
• 4360-47-8 cinnamonitrile 

Relevant academic research and scientific papers

Niacin as a Potent Organocatalyst towards the Synthesis of Quinazolines Using Nitriles as C–N Source

An efficient and cost-effective Vitamin-B3-catalyzed protocol towards the synthesis of diversely substituted quinazolines is illustrated using 2-aminobenzylamines and nitriles as substrates. An organocatalytic transformation has been investigat

Divergent Synthesis of Quinazolines Using Organocatalytic Domino Strategies under Aerobic Conditions

An easy and efficient organocatalytic approach to the synthesis of 2-substituted quinazolines is described based on the reaction between 2-aminobenzylamines and aldehydes or alcohols or amines. Three organocatalytic platforms were investigated, using 3-nitropyridine, pyridine N-oxide, and vitamin B3. Having established the new catalytic systems, the tandem transformations of 2-aminobenzylamines to give substituted quinazolines were achieved in excellent yields and with a broad substrate scope, with no formation of toxic side-products. The investigated conditions are not restricted to the use of aldehydes; the protocol also works well with alcohols or amines as substrates. These are oxidized in situ to the corresponding aldehydes to achieve the successful transformation. A mechanistic proposal has been drawn up based on control experiments. We found that under aerobic conditions, catalytic amounts of H2O2 can be generated; this plays a key role in the efficacy of the described approach. The green chemistry metrics of the developed method are also presented. The E factor of 8.18 mg/1 mg demonstrates that the reported method is an excellent complement to previous protocols.

A facile and versatile protocol for the one-pot PhI(OAc)2 mediated divergent synthesis of quinazolines from 2-aminobenzylamine

In this present work iodobenzenediacetate (PIDA) has been found to be the key reagent in absence or presence of catalytic amount of molecular iodine (I2)/zinc chloride (ZnCl2) to construct quinazoline scaffold from 2-aminobenzylamine and a variety of easily available aldehydes, aryl and aliphatic amines, aliphatic and aryl alcohols and nitriles. This protocol provides mild and robust conditions along with great versatility to synthesize 2-substituted quinazolines from diverse starting materials in good to excellent yields. The developed protocol is also well applicable to reactants containing ease to oxidation prone functional groups.

Quinazoline-Directed C–H Bond Functionalization Catalyzed by Ruthenium(II) Carboxylate – Construction of Polyconjugated Aryl-Heteroaryl Systems

A series of coupling products have been prepared by a ruthenium(II)-catalyzed direct ortho-C–H arylation of 2-(aryl/heteroaryl)-substituted quinazolines with (hetero)aryl bromides. Tri(hetero)aryl-substituted alkenes were also prepared by olefinic C–H activation of 2-(2-arylvinyl)quinazoline derivatives. High conversions and selectivities were achieved by choosing the appropriate ruthenium(II) carboxylate catalyst system, solvent, and reaction temperature. The possibility of a C(sp3)–H functionalization by applying an arylation/reduction reaction sequence was also demonstrated.

Oxidative olefination of secondary amines with carbon nucleophiles

An unprecedented olefination reaction of secondary amines with carbon nucleophiles has been developed through C-N/C-H functionalization under metal-free oxidative conditions. In the presence of a stoichiometric amount of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ), a range of secondary N-alkylanilines smoothly underwent oxidative olefination with 2-alkylazaarenes, acetophenone, and malononitrile to give structurally diverse polysubstituted alkenes in moderate to excellent yields with excellent (E) selectivity. Preliminary mechanistic studies revealed that the oxidative olefination reaction proceeds through amine oxidation followed by imine olefination. A range of secondary N-alkylanilines smoothly underwent DDQ-promoted oxidative olefination with 2-alkylazaarenes, acetophenone, and malononitrile to give structurally diverse alkenes in moderate to excellent yields with excellent (E) selectivity. Mechanistically, the reaction proceeds through amine oxidation followed by imine olefination (DDQ = 2,3-dichloro-5,6-dicyano-1,4-benzoquinone). Copyright

CuCl/DABCO/4-HO-TEMPO-catalyzed aerobic oxidative synthesis of 2-substituted quinazolines and 4 H -3,1-benzoxazines

The Cu/N-ligand/TEMPO catalytic system was first applied to the aerobic oxidative synthesis of heterocycles. As demonstrated, 2-substituted quinazolines and 4H-3,1-benzoxazines were synthesized efficiently from the one-pot reaction of aldehydes with 2-aminobenzylamines and 2-aminobenzyl alcohols, respectively, by employing CuCl/DABCO/4-HO-TEMPO as the catalysts and oxygen as the terminal oxidant.

Highly efficient one-pot synthesis of 2-substituted quinazolines and 4H-benzo[d][1,3]oxazines via cross dehydrogenative coupling using sodium hypochlorite

This communication describes a catalyst-free synthesis of 2-substituted quinazolines and 4H-benzo[d][1,3]oxazines using commericially available sodium hypochlorite as oxidant. Operational simplicity, mild reaction conditions and the ability to construct structurally diverse 2-quinazolines and 2-substituted 4H-benzo[d][1,3]oxazines by this method render it to be a practical alternative for the synthesis of these heterocycles.