25688-25-9

Usage

Appearance

Yellow to orange solid

Molecular weight

238.24 g/mol

Usage

Synthesis of pharmaceuticals, agrochemicals, and dyes; potential biological and pharmacological activities (anti-proliferative and antimicrobial properties)

Importance

Useful building block in organic synthesis; key intermediate in the preparation of various functionalized indole derivatives; valuable tool in medicinal and organic chemistry.

Upstream product

• 1493-27-2 ortho-nitrofluorobenzene 
• 120-72-9 indole 
• 146384-56-7 1-((4-chlorophenyl)sulfonyl)-1H-indole 
• 1160170-25-1 N-(4-ethylbenzene)sulfonylindole 
• 40899-71-6 1-benzenesulfonylindole 
• 31271-90-6 1-(p-toluenesulfonyl)-1H-indole 
• 88-73-3 2-Chloronitrobenzene 
• 577-19-5 2-nitrophenyl bromide 
• 609-73-4 o-nitroiodobenzene 

Downstream Products

• 473918-48-8 N-(2-aminophenyl)indole 
• 1134136-38-1 6-(4-nitrophenyl)indolo[1,2-a]quinoxaline 
• 1134136-36-9 N-(4-indolo[1,2-a]quinoxalin-6-ylphenyl)dimethylamine 
• 1134136-34-7 6-phenylindolo[1,2-a]quinoxaline 
• 1134136-40-5 6-(4-bromophenyl)indolo[1,2-a]quinoxaline 
• 1574323-96-8 (indolo[1,2-a]quinoxalin-6-yl)(phenyl)methanone 
• 1246861-59-5 6-methyl-6-phenyl-5,6-dihydroindolo[1,2-a]quinoxaline 

Relevant academic research and scientific papers

Palladium-Catalyzed Regioselective Synthesis of 1,2-Fused Indole-Diazepines via [5+2] Annulation of o-Indoloanilines with Alkynes

An efficient and regioselective palladium(II)-catalyzed [5+2] annulation of unprotected o-indoloanilines with internal alkynes under microwave irradiation has been explored. The diverse imine-containing 1,2-fused indole[1,7-a]diazepines are constructed in moderate to excellent yields. The mechanistic pathway shows pivalic acid and molecular oxygen to play crucial roles for the regeneration of highly active electrophilic palladium species in the catalytic cycle. (Figure presented.).

A novel construction of acetamides from rhodium-catalyzed aminocarbonylation of DMC with nitro compounds

Dimethyl carbonate (DMC), an environment-friendly compound prepared from CO2, shows diverse reactivities. In this communication, an efficient procedure using DMC as both a C1 building block and solvent in the aminocarbonylation reaction with nitro compounds has been developed. W(CO)6acts both a CO source and a reductant here.

Cobalt-Catalyzed Direct C-H Carbonylative Synthesis of Free (NH)-Indolo[1,2- a]quinoxalin-6(5 H)-ones

A cobalt-catalyzed direct C-H carbonylative reaction of N-(2-(1H-indol-1-yl)phenyl)picolinamides for the synthesis of (NH)-indolo[1,2-a]quinoxalin-6(5H)-one skeletons has been developed. Using benzene-1,3,5-triyl triformate (TFBen) as the CO source and picolinamide as the traceless directing group, various free (NH)-indolo[1,2-a]quinoxalin-6(5H)-ones were obtained in good yields (up to 88%). Additionally, a series of product derivatizations were demonstrated, and the core fragment of PARP-1 inhibitor C can be readily constructed by this protocol.

Synthesis of oxazolidinones through ring-opening and annulation of vinylene carbonate with 2-pyrrolyl/indolylanilines under Rh(iii) catalysis

Herein, we have developed a rhodium-catalyzed C-H functionalization and subsequent intramolecular ring-opening/cyclization of vinylene carbonate with 2-pyrrolyl/indolylanilines, which leads to oxazolidinones in moderate to good yields. In this transformation, vinylene carbonate only eliminates one oxygen atom rather than -CO3 or CO2. Furthermore, some control experiments are conducted to elucidate the reaction mechanism. This journal is

Mo–Catalyzed One-Pot Synthesis of N-Polyheterocycles from Nitroarenes and Glycols with Recycling of the Waste Reduction Byproduct. Substituent-Tuned Photophysical Properties

A catalytic domino reduction–imine formation–intramolecular cyclization–oxidation for the general synthesis of a wide variety of biologically relevant N-polyheterocycles, such as quinoxaline- and quinoline-fused derivatives, and phenanthridines, is reported. A simple, easily available, and environmentally friendly dioxomolybdenum(VI) complex has proven to be a highly efficient and versatile catalyst for transforming a broad range of starting nitroarenes involving several redox processes. Not only is this a sustainable, step-economical as well as air- and moisture-tolerant method, but also it is worth highlighting that the waste byproduct generated in the first step of the sequence is recycled and incorporated in the final target molecule, improving the overall synthetic efficiency. Moreover, selected indoloquinoxalines have been photophysically characterized in cyclohexane and toluene with exceptional fluorescence quantum yields above 0.7 for the alkyl derivatives.

Tin(ii) chloride dihydrate/choline chloride deep eutectic solvent: Redox properties in the fast synthesis of: N -arylacetamides and indolo(pyrrolo)[1,2- a] quinoxalines

In this contribution a physicochemical, IR and Raman characterization for the tin(ii) chloride dihydrate/choline chloride eutectic mixture is reported. The redox properties of this solvent were also studied by cyclic voltammetry finding that it can be successfully used as an electrochemical solvent for electrosynthesis and electroanalytical processes and does not require negative potentials as verified by the reduction of nitrobenzene. The potential use of this eutectic mixture as a redox solvent was further explored in obtaining aromatic amines and N-arylacetamides starting from a wide variety of nitroaromatic compounds. In addition, a fast synthetic strategy for the construction of a series of indolo(pyrrolo)[1,2-a]quinoxalines was developed by reacting 1-(2-nitrophenyl)-1H-indole(pyrrole) with aldehydes. This simple protocol offers a straightforward method for the construction of the target quinoxalines in short reaction times and high yields where the key step involves a tandem one-pot reductive cyclization-oxidation.

Organic compound based on nitrogen-containing fused ring and application thereof

The invention relates to the field of electroluminescent materials, and in particular relates to an organic compound based on a nitrogen-containing fused ring and application thereof. The organic compound has a structure as shown in structural formula (1)

Ruthenium-Catalyzed Synthesis of Pyrrolo[1,2- A [quinoxaline Derivatives from 1-(2-Aminophenyl)pyrroles and Sulfoxonium Ylides

A ruthenium-catalyzed [5+1] annulation of 1-(2-aminophenyl)pyrroles with α-carbonyl sulfoxonium ylides is reported. This reaction provides a one-step method for synthesizing pyrrolo[1,2- A [quinoxaline derivatives under ambient conditions. The system proceeds with a short reaction time and a high functional-group tolerance. Notably, this divergent protocol tolerates β-keto sulfoxonium ylides and can be applied to α-ester sulfoxonium ylides. A preliminary study was made of the mechanism of the reaction, and a reaction pathway is proposed.

Organic electroluminescent compound and application thereof

The present invention discloses an organic electroluminescent compound. A structural formula of the compound is as shown in a formula I or formula II. The compound is used as a material for an organicelectroluminescent element, and thereby a material for

Unexpected activated carbon-catalyzed pyrrolo[1,2-a]quinoxalines synthesis in water

An interesting and recyclable activated carbon/water catalytic system for efficient synthesis of pyrrolo[1,2-a]quinoxaline derivatives was developed. The intramolecular C–N and C–C bond can be easily constructed in water under mild condition. This reaction features a broad substrate scope, a good tolerance to water and air, metal-free, additive-free and redox reagent-free.