57707-16-1

Upstream product

• 57707-10-5 4-((2-nitrobenzylidene)amino)benzonitrile 
• 2863-98-1 4-hydrazinobenzonitrile hydrochloride 
• 873-74-5 4-Aminobenzonitrile 
• 271-44-3 benzimidazole 
• 1194-02-1 4-fluorobenzonitrile 
• 623-03-0 4-Cyanochlorobenzene 
• 623-00-7 4-bromobenzenecarbonitrile 
• 552-89-6 2-nitro-benzaldehyde 
• 3058-39-7 4-iodobenzonitrile 
• 3433-80-5 1-Bromo-2-bromomethyl-benzene 

Downstream Products

• 205309-86-0 2-(4-cyanophenyl)indazoline 

Relevant academic research and scientific papers

Manganese-Catalyzed Electrochemical Tandem Azidation-Coarctate Reaction: Easy Access to 2-Azo-benzonitriles

A one-pot cascade transformation consisting of an electrochemically driven azidation of 2H-indazole followed by coarctate fragmentation is developed to synthesize the 2-azo-benzonitrile motif. This manganese-catalyzed transformation is external-chemical-oxidant-free and operates at ambient temperature under air. This methodology exhibits good functional group tolerance, affording a broad range of substrate scopes of up to 89% isolated yield. Diverse derivatization of the 2-azo-benzonitrile product resulted in other valuable scaffolds.

Design, synthesis and anticandidal evaluation of indazole and pyrazole derivatives

Candidiasis, caused by yeasts of the genus Candida, is the second cause of superficial and mucosal infections and the fourth cause of bloodstream infections. Although some antifungal drugs to treat candidiasis are available, resistant strains to current therapies are emerging. Therefore, the search for new candicidal compounds is certainly a priority. In this regard, a series of indazole and pyrazole derivatives were designed in this work, employing bioisosteric replacement, homologa-tion, and molecular simplification as new anticandidal agents. Compounds were synthesized and evaluated against C. albicans, C. glabrata, and C. tropicalis strains. The series of 3-phenyl-1H-indazole moiety (10a–i) demonstrated to have the best broad anticandidal activity. Particularly, compound 10g, with N,N-diethylcarboxamide substituent, was the most active against C. albicans and both miconazole susceptible and resistant C. glabrata species. Therefore, the 3-phenyl-1H-indazole scaf-fold represents an opportunity for the development of new anticandidal agents with a new chemo-type.

A General One-Pot Synthesis of 2H-Indazoles Using an Organophosphorus–Silane System

A simple and direct approach for the regioselective construction of the privileged 2H-indazole scaffold is described. The developed one-pot strategy involves phospholene-mediated N?N bond formation to access 2H-indazoles. The amount of organophosphorus reagent was minimized by recycling the phospholene oxide with organosilane reductants. Starting from functionalized 2-nitrobenzaldehydes and primary amines, a mild reductive cyclization, involving the use of commercially available phospholene oxide and silanes, delivered a wide variety of substituted 2H-indazoles in good to excellent yields.

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 mild and regioselective Ullmann reaction of indazoles with aryliodides in water

A mild and regioselective Ullmann reaction of indazoles with aryliodides has been developed as a general method for the synthesis of 1-aryl-1H-indazoles. Water was used as the solvent wherein Tween 20 (2% w/w) was added to form aqueous micelles to improve

Gold modified zeolite: An efficient heterogeneous catalyst for n-arylation of indazole

We herein report N-arylation of indazole with aryl halides using gold modified zeolites (Au-zeolites) as an efficient catalytic system. Au-zeolites with three different gold loading were prepared by ion-exchange method and characterized by UV-visible diffuse reflectance spectroscopy (UV-DRS), transmission electron microscopy and energy-dispersive X-ray spectroscopy (TEM-EDX) and X-ray photoelectron spectroscopy (XPS). The Brunauer-Emmett-Teller (BET) and Langmuir surface areas of the prepared Au(5)-zeolite catalyst were found to be 644 and 929 m2g-1 respectively. Goldmodified zeolites performed as an efficient catalytic system for N-arylation of indazole using diverse aryl halides afforded N1 arylated products in appreciable yield under mild reaction conditions. The catalyst was reusable for at least five times with only a marginal loss of activity. This simple, effective and environmentally benign heterogeneous protocol provides a safer alternative to hazardous, corrosive and more polluting conventional catalysts.

Preparation of polyfunctional indazoles and heteroarylazo compounds using highly functionalized zinc reagents

Readily available 2-chloromethylarylzinc reagents react with functionalized aryldiazonlum tetrafluoroborates providing polyfunctional indazoles. Selective metalations of these 2-aryl-2H-indazoles afford new polycyclic aromatlcs. The performance of a chemo

A novel synthesis of 2-aryl-2H-indazoles via a palladium-catalyzed intramolecular amination reaction.

[reaction: see text] A variety of 2-aryl-2H-indazoles were synthesized by the palladium-catalyzed intramolecular amination of the corresponding N-aryl-N(o-bromobenzyl)hydrazines. Of several sets of reaction conditions surveyed, the combination of Pd(OAc)2

Synthesis and electrochemical behaviour of 2-N-substituted indazoles

A new 2-N-aryl-3-methoxycarbonylindazole synthesis from the 6 F mol-1 reduction of appropriately substituted aryl-nitrones has been developed. The indazoles bearing an electron withdrawing group in the 2-position are electroreducible compounds at high negative potentials producing selectively the corresponding 2-N-substituted indazolines in aqueous alcoholic medium. The nitrile and ester groups are not reduced under the reaction conditions. Three new 2-N-arylindazolines were synthesized and characterized. A second electron withdrawing group attached at the 3-position leads to a less cathodic reduction of the 2-N-aryl-3-methoxycarbonylindazole. An appropriately substituted indazoline was used to generate in situ a new tetracyclic heterocycle.

2-substituted indazoles from electrogenerated ortho-nitrosobenzylamines

An electrochemical methodology for an efficient access to ortho- nitrosobenzylamines has been developed. These products cyclize intramolecularly producing the desired 2-substituted indazoles in high yields. The electrochemical procedure overcomes limitations of previous chemical methods.