27895-77-8

Upstream product

• 75-31-0 isopropylamine 
• 552-89-6 2-nitro-benzaldehyde 
• 17064-86-7 N-(2-nitrobenzylidene)-4-nitroaniline 

Downstream Products

• 338991-54-1 N-isopropyl-2-nitrobenzylamine 
• 57707-13-8 2-isopropyl-2H-indazole 

Relevant academic research and scientific papers

Facile synthesis of 4-substituted 1,2,4,5-tetrahydro-1,4-benzodiazepin-3-ones by reductive cyclization of 2-chloro-N-(2-nitrobenzyl)acetamides

A facile and efficient method was developed for the synthesis of 1,2,4,5-tetrahydro-1,4-benzodiazepine-3-ones from 2-chloro-N-(2-nitrobenzyl)acetamides through a reductive cyclization using iron-ammonium chloride in ethanol–water in good yields. This method provides a simple approach to these benzodiazepine-3-ones which are of high value in the field of medicinal chemistry research.

A Biphilic Phosphetane Catalyzes N-N Bond-Forming Cadogan Heterocyclization via PIII/PV = O Redox Cycling

A small-ring phosphacycle, 1,2,2,3,4,4-hexamethylphosphetane, is found to catalyze deoxygenative N-N bond-forming Cadogan heterocyclization of o-nitrobenzaldimines, o-nitroazobenzenes, and related substrates in the presence of hydrosilane terminal reductant. The reaction provides a chemoselective catalytic synthesis of 2H-indazoles, 2H-benzotriazoles, and related fused heterocyclic systems with good functional group compatibility. On the basis of both stoichiometric and catalytic mechanistic experiments, the reaction is proposed to proceed via catalytic PIII/PV = O cycling, where DFT modeling suggests a turnover-limiting (3+1) cheletropic addition between the phosphetane catalyst and nitroarene substrate. Strain/distortion analysis of the (3+1) transition structure highlights the controlling role of frontier orbital effects underpinning the catalytic performance of the phosphetane.

Regioselective synthesis of 2 H-indazoles using a mild, one-pot condensation-cadogan reductive cyclization

An operationally simple and efficient one-pot synthesis of 2H-indazoles from commercially available reagents is reported. Ortho-imino-nitrobenzene substrates, generated via condensation, undergo reductive cyclization promoted by tri-n-butylphosophine to afford substituted 2H-indazoles under mild reaction conditions. A variety of electronically diverse ortho-nitrobenzaldehydes and anilines were examined. To further extend the scope of the transformation, aliphatic amines were also employed to form N2-alkyl indazoles selectively under the optimized reaction conditions.

Transimination reactions in [b-3C-im][NTf2] ionic liquid

Compared to conventional molecular solvents, the ionic liquid [b-3C-im][NTf2] was found to promote transimination reactions with up to ～100-fold rate enhancement. This rate effect observed at ambient temperature might be explained by the fact that the ionic liquid displays weak Lewis acidity with very low, if any, nucleophilicity and its imidazolium cation is expected to interact by associating with, and thus electrophilically activating, the CN bond of the starting imine, leading to increased stabilization of the polar, charged intermediate species and ultimately, rapid product formation. Moreover, the presence of 1 mol% Sc(OTf)3 in [b-3C-im][NTf2] further facilitates the transimination reactions studied.

Palladium Complex-Catalyzed Reductive N-Heterocyclization of Nitroarenes: Novel Synthesis of Indole and 2H-Indazole Derivatives

The dichlorobis(triphenylphosphine)palladium (PdCl2(PPh3)2)-tin(II)chloride (SnCl2) system shows high catalytic activity for the reductive N-heterocyclization of various 2-nitrostyrene and N-(2-nitrobenzylidene)amine derivatives when employed at 100 deg C for 16 h under 20 kg cm-2 of initial carbon monoxide pressure, to give the corresponding indole and 2H-indazole derivatives in good yield.For example, 2-phenylindole was obtained in 75percent yield from the reductive N-heterocyclization of 2-nitrostilbene.Similarly, 2-propyl-2H-indazole was readily prepared in 83percent yield by the reductive N-heterocyclization of N-(2-nitrobenzylidene)propylamine.A nitrene intermediate for the present reaction is proposed on the basis of deuterium-labeling experiments and the investigation of alkyl rearrangement in the construction of the indole skeleton.Carbon monoxide effectively operates as a deoxygenating agent of the nitro group to afford a nitrene intermediate.