6141-98-6

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 25, p. 736, 1960 DOI: 10.1021/jo01075a016Tetrahedron Letters, 34, p. 877, 1993 DOI: 10.1016/0040-4039(93)89037-Q

InChI:InChI=1/C12H8N2O/c15-14-12-8-4-2-6-10(12)9-5-1-3-7-11(9)13-14/h1-8H

Upstream product

• 2436-96-6 1-nitro-2-(2-nitrophenyl)benzene 
• 7052-12-2 benzo[c]cinnoline-N,N'-dioxide 
• 35883-86-4 2-amino-2'-nitrobiphenyl 
• 56-81-5 glycerol 
• 29722-92-7 2'-nitro-biphenyl-2-carboxylic acid amide 
• 98-95-3 nitrobenzene 
• 62-53-3 aniline 
• 95-51-2 o-chloroaniline 
• 13463-40-6 iron pentacarbonyl 
• 71237-36-0 2'-nitrobiphenyl acid chloride 
• 17294-89-2 2'-nitro-biphenyl-2-carboxylic acid 
• 17613-50-2 (2'-nitro-biphenyl-2-yl)-carbamic acid ethyl ester 
• 230-17-1 benzo[c]cinnoline 

Downstream Products

• 230-17-1 benzo[c]cinnoline 
• 81709-93-5 7-(Octahydro-9aH-trans-benzocycloocta<3,4>pyrazolo<1,2-a>cinnolin-16-yl)heptanal 
• 60-80-0 antipyrine 
• 1620101-19-0 4-(4-methylphenylsulfonamido)benzo[c]cinnoline 5-oxide 
• 854637-47-1 N-benzo[c]cinnolin-2-yl-N-(2-diethylamino-ethyl)-toluene-4-sulfonamide 
• 854637-54-0 N-benzo[c]cinnolin-2-yl-toluene-4-sulfonamide 
• 4827-07-0 2-Amino-benzocinnolin 
• 7090-45-1 octachlorobiphenylene 
• 259-79-0 bisbenzocyclobutene 

Relevant academic research and scientific papers

A practical synthesis of substituted benzo[c]cinnoline- N,N′-dioxides and N-oxides

A practical synthesis of variously substituted benzo[c]cinnoline-N,N′-dioxides and N-oxides is described, based on the reduction of the appropriate o,o′-dinitrobiphenyl compound with KOH in refluxing 2-propanol.

Chemoselective electrochemical reduction of nitroarenes with gaseous ammonia

Valuable aromatic nitrogen compounds can be synthesized by reduction of nitroarenes. Herein, we report electrochemical reduction of nitroarenes by a protocol that uses inert graphite felt as electrodes and ammonia as a reductant. Depending on the cell voltage and the solvent, the protocol can be used to obtain aromatic azoxy, azo, and hydrazo compounds, as well as aniline derivatives with high chemoselectivities. The protocol can be readily scaled up to >10 g with no decrease in yield, demonstrating its potential synthetic utility. A stepwise cathodic reduction pathway was proposed to account for the generations of products in turn.

NOVEL PREPARATION METHOD OF QUINOLINE N-OXIDE DERIVATIVE WITH AMIDE GROUP

Provided are a preparation method of a quinoline N-oxide derivative with an amide group capable of easily introducing the amide group into the quinoline N-oxide derivative by simplified processes and mild reaction conditions, and a quinoline N-oxide derivative with an amide group prepared by using the same.

Transition-Metal-Free Cross-Coupling Reactions by Single Electron Transfer (SET)

A facile, efficient, single-step protocol for the synthesis of cinnoline derivatives by a transition-metal-free coupling between amino- and nitroaryl compounds by single electron transfer (SET) has been developed. Direct carbon-carbon bond formation was achieved from nonfunctionalized aromatic carbon atoms. A plausible mechanism has been proposed.

Transition-metal-free cross-coupling reactions by single electron transfer (SET)

A facile, efficient, single-step protocol for the synthesis of cinnoline derivatives by a transition-metal-free coupling between amino- and nitroaryl compounds by single electron transfer (SET) has been developed. Direct carbon-carbon bond formation was achieved from nonfunctionalized aromatic carbon atoms. A plausible mechanism has been proposed. Direct carbon-carbon bond formation between nonfunctionalized carbon atoms (C-H) in the presence of KOtBu for the synthesis of cinnoline derivatives was achieved. Copyright

Regioselective introduction of heteroatoms at the C-8 position of quinoline N-oxides: Remote C-H activation using N-oxide as a stepping stone

Reported herein is the metal-catalyzed regioselective C-H functionalization of quinoline N-oxides at the 8-position: direct iodination and amidation were developed using rhodium and iridium catalytic systems, respectively. Mechanistic study of the amidation revealed that the unique regioselectivity is achieved through the smooth formation of N-oxide-chelated iridacycle and that an acid additive plays a key role in the rate-determining protodemetalation step. While this approach of remote C-H activation using N-oxide as a directing group could readily be applied to a wide range of heterocyclic substrates under mild conditions with high functional group tolerance, an efficient synthesis of zinquin ester (a fluorescent zinc indicator) was demonstrated.

1,2-Eliminations in a novel reductive coupling of nitroarenes to give azoxy arenes by sodium bis(trimethylsilyl)amide

(Chemical Equation Presented) Symmetric azoxy arenes were successfully prepared in one step from 2 equiv of the corresponding nitroarenes by use of sodium bis-(trimethylsilyl)amide as the deoxygenating agents in THF at 150°C in a sealed tube.

Investigations of a novel process to the framework of benzo[c]cinnoline

A novel synthetic process leading to the framework of benzo[c]cinnoline has been discovered and investigated. The process is composed of two separate reactions, the first of which is a partial reduction of the nitro groups of the 2,2′-dinitrobiphenyl, a process that we believe proceeds via a SET mechanism to yield the hydroxyamino and nitroso groups. In the following step the cyclization takes place under formation of the -N=N- bond. We believe that this process take place via a radical mechanism through the nitroso radical anion. The novel process affords either benzo[c]cinnoline or benzo[c]cinnoline N-oxide, both in high yields, 93% and 91%, respectively. To obtain benzo[c]cinnoline, the reaction is conducted with an alcohol as solvent and an alkoxide as the base, while for benzo[c]cinnoline N-oxide, water is used as solvent with sodium hydroxide as the base. To establish the latter procedure, statistical experimental design and multivariate modeling were utilized to reveal the response surface for the reaction and to determine the optimal conditions for the reaction. A proposal for the complex reaction mechanism is given. During the corroboration of the mechanism, a new deoxygenation reaction for converting benzo[c]cinnoline N-oxide into benzo[c]cinnoline was discovered. The reaction is conducted by treating the N-oxide with sodium ethoxide at elevated temperature to achieve near-quantitative conversion into benzo[c]cinnoline in a yield of 96%.

The newborn surface of dull metals in organic synthesis. Bismuth-mediated solvent-free one-step conversion of nitroarenes to azoxy- and azoarenes

When milled together with bismuth shots, nitroarenes are readily converted to azoxy- and/or azoarenes depending on substrates and conditions employed. Simple extraction with organic solvent followed by evaporation of the resulting dark pasty solid gave the product in good yield.

Anti-androgenic activity of substituted azo- and azoxy-benzene derivatives.

Substituted phenylazo and phenylazoxy compounds were systematically prepared and their anti-androgenic activity was measured in terms of (1) the growth-inhibiting effect on an androgen-dependent cell line, SC-3, and (2) the binding affinity to nuclear androgen receptor. Generally, azo/azoxy compounds showed cell toxicity, and the growth-inhibiting effects on SC-3 cells correlated with the toxicity. However, some compounds, including 4,4'-dinitroazobenzene (25), 4,4'-dimethoxyazobenzene (33), and 2,2'-dichloroazoxybenzene (47), possessed potent anti-androgenic activity without apparent cell toxicity.