21258-59-3

Upstream product

• 107125-70-2 lithium N-phenyl-N-methylcarbamate 
• 103-71-9 phenyl isocyanate 
• 62-53-3 aniline 
• 13061-96-6 dihydroxy-methyl-borane 
• 4424-17-3 2-aminobenzanilide 
• 118-48-9 isatoic anhydride 
• 21563-73-5 2-aminobenzoyl chloride 
• 118-92-3 anthranilic acid 
• 74-88-4 methyl iodide 
• 201230-82-2 carbon monoxide 
• 100-61-8 N-methylaniline 
• 10328-92-4 N-Methylisatoic anhydride 
• 119515-87-6 o-bromo-N-methyl-N-allyloxyaniline 
• 119515-88-7 N-(2-bromophenyl)-N-methyl-O-propylhydroxylamine 

Downstream Products

• 92148-68-0 1-methyl-2-phenyl-1,2-dihydro-3H-imidazol-3-one 
• 16347-60-7 3-phenyl-4(3H)-quinazolinone 
• 1596243-51-4 1,3-dimethyl-2-phenyl-1,2,3,4-tetrahydroquinazoline 
• 16285-32-8 2,3-dihydro-3-methyl-2-phenylquinazolin-4(1H)-one 
• 35042-18-3 o-Methylamino-N-phenylbenzylamin 
• 100-52-7 benzaldehyde 
• 73302-18-8 1-methyl-2,3-diphenyl-2,3-dihydroquinazolin-4(1H)-one 
• 36384-00-6 1-methyl-3-phenyl-2,3-dihydroquinazolin-4(1H)-one 
• 55538-70-0 1-methyl-3-phenyl-2,3-dihydroquinazolin-4(1H)-one-2,2-d₂ 
• 17761-75-0 1,2-dimethyl-3-phenyl-2,3-dihydroquinazolin-4(1H)-one 
• 52462-89-2 2-(N-methylformamido)-N-phenylbenzamide 

Relevant academic research and scientific papers

Electrochemical utilization of methanol and methanol-d4 as a C1 source to access (deuterated) 2,3-dihydroquinazolin-4(1H)-one

Herein, an electrocatalytic protocol for the synthesis of 2,3-dihydroquinazolin-4(1H)-one has been disclosed. Methanol is activated and utilized as the C1 source to cyclize with 2-aminobenzamides. This cyclization reaction proceeds conveniently (room temperature and air atmosphere) without any homogeneous metal catalysts, external oxidants, or bases. A wide variety of N,N-disubstituted 2,3-dihydroquinazolin-4(1H)-ones are obtained via this approach. Moreover, when methanol-d4 is used, a deuterated methylene motif is incorporated into the N-heterocycles, providing an efficient approach to the deuterated N-heterocycles.

Copper-Catalyzed Oxidative Cyclization of 2-Aminobenzamide Derivatives: Efficient Syntheses of Quinazolinones and Indazolones

A simple copper-catalyzed assembly to formulate quinazolinone and indazolone derivatives in a single protocol manner is reported. These transformations are based on the fact that DMF can serve as a reaction solvent and one carbon synthon for the construct

NaNO2/I2 as an alternative reagent for the synthesis of 1,2,3-benzotriazin-4(3H)-ones from 2-aminobenzamides

An efficient transformation of 2-aminobenzamides to 1,2,3-benzotriazin-4(3H)-ones in the presence of sodium nitrite (NaNO2) and Iodine (I2) is described. The reaction is proposed to proceed via formation of nitrosyl halide that induces nitrosylation of the amino group of 2-aminobenzamide leading to diazotization followed by intramolecular cyclization.

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.

Palladium-Catalyzed Ortho-Selective C-H Oxidative Carbonylation of N-Substituted Anilines with CO and Primary Amines for the Synthesis of o-Aminobenzamides

An efficient, one-pot strategy with high selectivity and high atom economy for the synthesis of o-aminobenzamides has been developed via palladium-catalyzed ortho-selective C-H oxidative carbonylation of N-substituted anilines with CO and primary amines. A wide range of N-substituted anilines and primary amines can be tolerated in this transformation to afford the corresponding o-aminobenzamides in moderate to excellent yields under mild conditions.

Experimental and theoretical investigations into the stability of cyclic aminals

Background: Cyclic aminals are core features of natural products, drug molecules and important synthetic intermediates. Despite their relevance, systematic investigations into their stability towards hydrolysis depending on the pH value are lacking. Results: A set of cyclic aminals was synthesized and their stability quantified by kinetic measurements. Steric and electronic effects were investigated by choosing appropriate groups. Both molecular mechanics (MM) and density functional theory (DFT) based studies were applied to support and explain the results obtained. Rapid decomposition is observed in acidic aqueous media for all cyclic aminals which occurs as a reversible reaction. Electronic effects do not seem relevant with regard to stability, but the magnitude of the conformational energy of the ring system and pKa values of the N-3 nitrogen atom. Conclusion: Cyclic aminals are stable compounds when not exposed to acidic media and their stability is mainly dependent on the conformational energy of the ring system. Therefore, for the preparation and work-up of these valuable synthetic intermediates and natural products, appropriate conditions have to be chosen and for application as drug molecules their sensitivity towards hydrolysis has to be taken into account.

A novel catalyst zinc(II) perfluorooctanoate [Zn(PFO)2]-catalyzed three-component one-pot reaction: Synthesis of quinazolinone derivatives in aqueous micellar media

A new type of Lewis acid-surfactant-combined catalyst (LASC), zinc(II) perfluorooctanoate [Zn(PFO)2], was prepared and applied as a favorable surfactivity catalyst in three-component one-pot cyclocondensation reaction of isatoic anhydride with amines and aldehydes to afford the corresponding quinazolinone derivatives in good yields. Reactions occurred under aqueous micellar media in high atom economy. It was found that this catalyst could be easily quantitatively recovered after the reaction completed and could be reused for at least three cycles without any loss of activity. Furthermore, a mechanism to rationalize the reaction was proposed.

Novel alternative for the N-N bond formation through a PIFA-mediated oxidative cyclization and its application to the synthesis of indazol-3-ones

The synthesis of a series of N,N′-disubstituted indazolone derivatives starting from methyl anthranilates is presented. This general approach features a novel and easy way for access to the target N-heterocycles by formation of a new N-N single bond. The

A SYNTHETIC EQUIVALENT FOR ORTHO-LITHIO-N-METHYLANILINE

o-Bromo-N-methyl-N-n-propoxyaniline undergoes halogen-metal exchange with butyllithium and the resulting lithio species reacts cleanly with a variety of electrophiles.The N-O bond of these products can be reduced with Raney nickel to afford ortho-substituted-N-methylanilines.

Carbon Dioxide: A Reagent for the Simultaneous Protection of Nucleophilic Centres and the Activation of Alternative Locations to Electrophilic Attack. Prt III. A New Synthetic Method for the ortho-Substitution of N-Monoalkylanilines

N-Methyl- and N-ethyl-aniline are regiospecifically converted into a range of ortho-substituted derivatives, using carbon dioxide both for N-protection and as an intermediate carbanion stabilizing group, and t-butyllithium to lithiate the ortho-carbon atom.The rersulting lithium N-(ortho-substituted-phenyl)-N-methyl- and -N-ethylcarbamates undergo smooth acid-catalysed decarboxylation under mild conditions.No alpha-substituted products were detected.