14717-15-8

Usage

InChI:InChI=1/C13H10N2O2/c16-15(17)13-9-5-4-8-12(13)14-10-11-6-2-1-3-7-11/h1-10H/b14-10+

Upstream product

• 100-52-7 benzaldehyde 
• 88-74-4 2-nitro-aniline 
• 100-51-6 benzyl alcohol 

Downstream Products

• 17064-90-3 2-nitro-N-(3-nitro-benzyliden)-aniline 
• 538-51-2 benzylidene phenylamine 
• 141262-95-5 [(2-Nitro-phenylamino)-phenyl-methyl]-phosphonic acid diethyl ester 
• 716-79-0 2-phenyl-1H-benzoimidazole 
• 5729-06-6 N-benzyl-2-nitroaniline 
• 1044499-42-4 (S)-2-cyclohexyl-2,3-dihydroquinazolin-4(1H)-one 
• 1044499-41-3 (R)-2-phenyl-2,3-dihydroquinazolin-4(1H)-one 

Relevant academic research and scientific papers

Facile route for green synthesis of N-benzylideneaniline over bimetallic reduced graphene oxide: chemical reactivity of 2,3,4-substituted derivatives of aniline

Mn–Co-decorated reduced graphene oxide (Mn–Co–rGO) was prepared by modified condensation method and characterized through XRD, SEM, EDX, FTIR and BET surface area analysis. The prepared sample was explored for its activity in the synthesis of N-benzylideneaniline (N-BA) using benzyl alcohol and PhNH2 as precursors. The catalyst has been used efficiently with high activity and selectivity for oxidation of benzyl alcohol to benzaldehyde in the presence of molecular oxygen, which further react with aniline to produced N-BA with sustainable catalytic activity up to five cycles. Furthermore, the effect of the nature and position of the substituent on aniline on the chemical reactivity of the nucleophile was studied theoretically using density functional calculations.

Pd-Catalyzed Reductive Cyclization of Nitroarenes with CO2 as the CO Source

A reductive amination process that constructs indoles, carbazoles or benzimidazoles from nitroarenes – irrespective of their electronic or steric nature – was developed that uses CO2 as the source of CO. The process is robust, tolerating common gaseous components of flue gas (H2S, SO2, NO and H2O) without adversely affecting the reductive cyclization.

Palladium-Catalyzed Formation of N-Heteroarenes from Nitroarenes using Molybdenum Hexacarbonyl as the Source of Carbon Monoxide

The development of a method that employs a two-chamber reaction vessel and uses molybdenum hexacarbonyl [Mo(CO)6] as the carbon monoxide (CO) source for the palladium-catalyzed transformation of nitroarenes into indoles or imidazoles is reported.

Grinding synthesis of schiff bases combined with infrared irradiation

Solid-phase synthesis combined with infrared irradiation promoted the formation of a series of Schiff bases in the condensation reaction between substituted benzaldehydes and anilines, in the solvent free. Benzaldehydes and anilines, containing either electron withdrawing or electron-releasing groups, were evaluated their substituent effect on the formation of the Schiff bases. Moreover, this new procedure is environmentally benign because no solvent was employed in the transformations.

Catalytic asymmetric synthesis of dihydroquinazolinones from imines and 2-aminobenzamides

An unprecedented catalytic asymmetric synthesis of aminal-containing heterocyclic compounds has been developed from imines and tethered nitrogen/nitrogen nucleophiles. In the presence of 10mol% of a commercially available chiral phosphoric acid, a range of aromatic, α,β- unsaturated, and aliphatic imines react with 2-aminobenzamides to give dihydroquinazolinones in good to excellent yields and ee. The enantioselectivity is significantly affected by the imine N-substituent through non-bonding interactions with the chiral phosphoric acid and the 2-aminobenzamide. Copyright

Cytotoxic effects of new trans-2,4-diaryl-r-3-methyl-1,2,3,4- tetrahydroquinolines and their interaction with antitumoral drugs gemcitabine and paclitaxel on cellular lines of human breast cancer

Two tetrahydroquinoline compounds, called DM8 and DM12, from a new series of the cis-2,4-diaryl-r-3-methyl-1,2,3,4-tetrahydroquinolines, were selected for cytotoxic effects studies on cellular lines of human breast cancer. The synergistic, additive and an

Microwave-assisted Cadogan reaction for the synthesis of 2-aryl-2H-indazoles, 2-aryl-1H-benzimidazoles, 2-carbonylindoles, carbazole, and phenazine

(Chemical Equation Presented) The Cadogan reaction, a widely accepted route for the synthesis of nitrogen containing heterocycles, is modified by using microwave radiation as the source of heat instead of the conventional heating by reflux in a nitrogen atmosphere for several hours. Appropriate starting materials were mixed with triethyl phosphite or triphenylphosphine and irradiated with microwaves for several minutes at a specific power to give the desired products. The indazoles were prepared by irradiating N-(2-nitrobenzylidene) anilines with triethyl phosphite at 200 W for 12-14 min to give 85-92% product yields. Irradiation of the mixture of N-benzylidene-2-nitroanilines and triphenylphosphine at 200 W for 3-5 min yielded 93-96% of the benzimidazoles. The carbonylindoles were obtained in 61-68% yields by irradiating 2-nitrochalcone or alkyl 2-nitrocinnamates and triphenylphosphine with microwaves at 80-200 W for 8-11 min. The mixture of 2-nitrobiphenyl and triphenylphosphine yielded 96% of carbazole when irradiated with microwaves at 200 W for 2 min while 75% of phenazine was obtained by irradiating the mixture of 2-nitrodiphenylamine and triphenylphosphine with microwaves at 200 W for 3.5 min. These results show that microwave-assisted Cadogan reactions gave better product yields at shorter reaction times.

A new method for the synthesis of 2-aryl-1H-benzimidazoles: Selenium-catalyzed reductive N-heterocyclization of benzylidene(2-nitroaryl) amines with carbon monoxide

The treatment of benzylidene(2-nitroaryl)amines, prepared by the reaction of o-nitro aniline and benzaldehydes, with carbon monoxide in the presence of a catalytic amount of selenium under basic conditions, afforded 2-aryl-1H-benzimidazoles in moderate to good yields. Georg Thieme Verlag Stuttgart.

Hydrosilylation of (hetero)aromatic aldimines in the presence of a Pd(I) complex

The reaction of triethylsilane with heterocyclic and aromatic azomethines, catalyzed by the [Pd(allyl)Cl]2 complex, was studied. It was found that the reaction is affected by the nature of the functional groups in the aza and methine parts of the aldimine molecules, which were produced by the condensation of furan, thiophene, and benzene aldehydes with aniline and its derivatives. The reactivity of a series of imines is compared with their electronic and structural characteristics, determined by quantum-chemical methods. The corresponding furan, thiophene, and aromatic amines and also certain silylamines were synthesized.

An efficient synthesis of anilinobenzylphosphonates

An efficient one-pot synthesis of anilinobenzylphosphonates was achieved from the reaction of aniline, benzaldehyde, and dialkylphosphite in the presence of BF3·OEt2 as a catalyst