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 
• 134-20-3 2-carbomethoxyaniline 
• 80-43-3 bis(1-methyl-1-phenylethyl)peroxide 
• 118-48-9 isatoic anhydride 
• 107-11-9 1-amino-2-propene 
• 67-68-5 dimethyl sulfoxide 
• 119072-55-8 tert-butylisonitrile 

Downstream Products

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

Relevant academic research and scientific papers

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.

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

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