17064-89-0

Upstream product

• 106-40-1 4-bromo-aniline 
• 552-89-6 2-nitro-benzaldehyde 

Downstream Products

• 3682-74-4 2-(4-bromophenyl)-2H-indazole 
• 56156-69-5 (4-bromo-phenyl)-(3-methoxy-1-oxy-cinnolin-4-yl)-amine 
• 56156-74-2 2-(4-bromo-phenyl)-2H-indazole-3-carbonitrile 
• 109772-91-0 (4-Bromo-phenylamino)-(2-nitro-phenyl)-acetonitrile 
• 109772-98-7 2-(4-bromo-phenyl)-1-oxy-2H-indazole-3-carbonitrile 
• 945033-66-9 6-bromo-4-(triisopropylsilyl)methyl-2-(o-nitrophenyl)quinoline 
• 1204524-89-9 C₂₈H₂₀Br₂N₄O₂ 
• 1451218-02-2 1-(4-bromophenyl)-2-(2-nitrophenyl)-5-phenyl-1H-imidazole 
• 418784-56-2 4-bromo-N-(2-nitro-benzyl)-aniline 

Relevant academic research and scientific papers

Highly efficient yellow-emitting iridium(III) complexes based on fluorinated 2-(biphenyl-4-yl)-2H-indazole ligands: Syntheses, structures, properties, and density functional theory calculations

Two new iridium (III) complexes (Ir1-Ir2) bearing different fluorinated 2-(biphenyl-4-yl)-2H-indazole-based compounds as cyclometalated ligands and Xantphos as an ancillary ligand were synthesized and fully characterized. The ultraviolet (UV)–vis absorpti

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.

Novel strategy for the preparation of 3-perfluoroalkylated-2H-indazole derivatives

A simple and novel methodology for the synthesis of 3-perfluoroalkylated-2H-indazole derivatives has been elaborated. The perfluoroalkylation of readily available 2-nitrobenzaldimines bearing electron donating groups was performed using the Ruppert-Prakas

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.

A Facile One-Step Synthesis of 2-Arylindazoles via Reductive Cyclization of N-(2-nitroarylidene)amines

A mild and efficient synthesis of 2-arylindazole derivatives via the reductive cyclization of nitro-aryl substrates mediated by a low-valent titanium reagent (TiCl4/Sm/Et3N) has been developed. The attractive features of the current method include an N-N bond formation and the selective reduction of the =C-N bond and nitro group, both of which were easily achieved in one-pot by controlling the pH of the reaction mixture.

Oriented synthesis and in vitro anticancer activity of biquinazoline-2,2'- diones

The synthesis of a series of biquinazoline-2,2'-diones starting from o-nitrobenzaldehydes, anilines, and triphosgene is presented. This general approach features a novel and easy way for access to the target products. The mechanistic course of the reaction suggests the involvement of reduction, coupling, and cyclization by one-pot. These compounds were also investigated in vitro for anticancer activity, and some were found to have good anticancer activity.

o-Nitrobenzylidene Compounds. Part 3. Formation of 4-Arylamino-3-methoxycinnoline 1-Oxides from N-o-Nitrobenzylideneanilines, Cyanide Ion, and Methanol: the Intermediacy of 2-Aryl-3-cyano-2H-indazole 1-Oxides

The N-o-nitrobenzylidene derivatives of variously substituted anilines (7) have been cyclised by potassium cyanide in methanol, to give 4-arylamino-3-methoxycinnoline 1-oxides (9), the structures of which have been confirmed by independent synthesis of one representative .These cinnoline oxides are the main products (sometimes the only isolated products) when the amine-derived ring in (7) is ortho-substituted; in other cases the cinnoline oxides are minor products formed along with 2-aryl-3-cyano-2H-indazoles (10).In the latter group of reactions, the primary cyclisation products are 2-aryl-3-cyano-2H-indazole 1-oxides (8): these have then either been reduced to the indazoles in the basic methanolic medium, or have undergone ring-opening and recyclisation to give the cinnoline oxides (9).In the other group, where indazole oxides (8) cannot usually be isolated, their intermediacy in cinnoline oxide formation remains a possibility, although other mechanistic pathways can be envisaged.Some 'borderline' cases are identified and discussed.