16899-50-6

Upstream product

• 64-18-6 formic acid 
• 4943-85-5 2-amino-N-(2-methylphenyl)benzamide 
• 118-92-3 anthranilic acid 
• 122-51-0 orthoformic acid triethyl ester 
• 95-53-4 o-toluidine 
• 149-73-5 trimethyl orthoformate 
• 62303-06-4 N-(2-methylphenyl)-o-iodobenzamide 
• 3473-63-0 formamidine acetic acid 
• 119072-55-8 tert-butylisonitrile 
• 107-21-1 ethylene glycol 
• 298-12-4 Glyoxilic acid 
• 1895-39-2 sodium chlorodifluoroacetate 
• 67-68-5 dimethyl sulfoxide 
• 107-11-9 1-amino-2-propene 

Downstream Products

• 127662-25-3 3-o-tolyl-1,2,3,4-tetrahydro-quinazoline 
• 72-44-6 methaqualone 

Relevant academic research and scientific papers

Transition-metal and oxidant-free approach for the synthesis of diverse N-heterocycles by TMSCl activation of isocyanides

A highly efficient TMSCl-mediated addition of N-nucleophiles to isocyanides has been achieved. This transition-metal and oxidant-free strategy has been applied to the construction of various N-heterocyles such as quinazolinone, benzimidazole and benzothiazole derivatives by the use of distinct amino-based binucleophiles. The notable feature of this protocol includes its mild reaction condition, broad functional group tolerance and excellent yield. This journal is

Metal-free C-H methylation and acetylation of heteroarenes with PEG-400

The generation of a methyl carbon source from renewable and cheap sources is challenging. Herein, we describe a novel and an efficient route for methylation and acetylation of aza-heteroarenes using PEG-400 under O2and TsOH·H2O for the first time by tuning the reaction conditions using a different set of starting materials. The key features of the current protocol are oxidative C-O and C-C bond scission under metal-free conditions with good functional group tolerance, and a broad substrate scope. The potential applicability of the designed methodology was demonstrated for the synthesis of central nervous system (CNS) depressant and anticonvulsant drug molecules by a one-pot strategy.

New Strategy for the Synthesis of Heterocycles via Copper-Catalyzed Oxidative Decarboxylative Amination of Glyoxylic Acid

A copper-catalyzed oxidative decarboxylative amination of glyoxylic acid with substrates having two nitrogen-nucleophilic sites was first demonstrated. Using this novel approach, 1,3,5-triazines, quinazolinones and quinazolines were obtained in up to 93 % yields. Notably, glyoxylic acid was employed as the C1 synthon for heterocycles. This strategy enriches the application of glyoxylic acid for the synthesis of valuable heterocycles.

Transition metal-free C-F/C-Cl/C-C cleavage of ClCF2COONa for the synthesis of heterocycles

A transition metal-free and external oxidant-free annulation of substrates having two nitrogen-nucleophilic sites with ClCF2COONa was demonstrated, affording a series of 1,3,5-triazines and quinazolinones in up to 96% yields. Notably, ClCF

Transition metal-free synthesis of quinazolinones using dimethyl sulfoxide as a synthon

Biologically important quinazolinones have been synthesized from 2-aminobenzamides and DMSO. The key feature of the reaction is the utilization of DMSO as a methine source for intramolecular oxidative annulation. The CNS depressant drug methaqualone has also been synthesized by our methodology. The present method involves the synthesis of quinazolinones with a broad substrate scope and a good yield.

Furan-2-carbaldehydes as C1 building blocks for the synthesis of quinazolin-4(3: H)-ones via ligand-free photocatalytic C-C bond cleavage

Furan-2-carbaldehydes, as biomass-derived chemicals, are used as efficient green C1 building blocks to synthesize bioactive quinazolin-4(3H)-ones by ligand-free photocatalytic C-C bond cleavage. Notably, protection of hydroxyl, carboxyl, amide, or secondary amino groups is not required. Mechanistic studies suggest that conjugated N,O-tridentate copper complexes act as novel photoinitiators under visible light.

Synthesis of 2,3-Disubstituted Quinazolinone Derivatives through Copper Catalyzed C-H Amidation Reactions

The synthesis of quinazolinone derivatives was achieved from 2-iodobenzamide derivatives and various benzylamines, allylamine, and cinnamylamine derivatives through a one-pot copper-catalyzed reaction. In this reaction, the amine component (benzylamine/allylamine/cinnamylamine) is N-arylated with 2-iodobenzamide derivatives through Ullman coupling, followed by an intramolecular C-H amidation in the presence of copper catalyst. Copper-catalyzed tandem-Ullman N-alkylation and intramolecular C-H amidation reaction protocol for the synthesis of 2-phenylquinazolinone and quinazolinone derivatives from N-substituted 2-iodo-benzamides and benzylamines, allyl, and cinnamylamine is achieved.

Copper-catalyzed radical methylation/C-H amination/oxidation cascade for the synthesis of quinazolinones

A copper-catalyzed radical methylation/sp3 C-H amination/oxidation reaction for the facile synthesis of quinazolinone was developed. In this cascade reaction, dicumyl peroxide acts not only as a useful oxidant but also as an efficient methyl source. Notably, a methyl radical, generated from peroxide, was confirmed by electron paramagnetic resonance for the first time.

Ammonium chloride-catalyzed one-pot synthesis of 4(3H)-quinazolinones under solvent-free conditions

Ammonium chloride, which is a very inexpensive and readily available reagent, can efficiently catalyze three-component, one-pot condensation reactions of 2-amino-benzoic acid esters, ortho esters, and aromatic amines to afford the corresponding 4(3H)-quinazolinones in good to excellent yields under solvent-free conditions.

Aluminium nitrate-catalyzed one-pot synthesis of 4(3h)-quinazolinones by a three-component coupling of anthranilic acid, amines, and ortho esters

The one-pot synthesis of quinazolinone derivatives from the reaction of anthranilic acid, amines, and ortho esters in the presence of aluminium nitrate has been carried out. The reaction occurred in a few minutes at room temperature under solvent-free con