870072-59-6

Upstream product

• 83-34-1 3-Methylindole 
• 615-43-0 2-iodophenylamine 
• 1493-27-2 ortho-nitrofluorobenzene 
• 88-74-4 2-nitro-aniline 
• 1045601-63-5 3-methyl-1-(2-nitro-phenyl)-1H-indole 

Downstream Products

• 32464-46-3 7-methyl-6-phenyl-indolo[1,2-a]quinoxaline 
• 1355019-83-8 4-methyl-N-(2-(3-methyl-1H-indol-1-yl)phenyl)benzenesulfonamide 
• 1360546-79-7 6-(4-bromophenyl)-7-methylindolo[1,2-a]quinoxaline 
• 1360546-75-3 6-(3-chlorophenyl)-7-methylindolo[1,2-a]quinoxaline 
• 1360546-68-4 6-(3-chlorophenyl)-7-methyl-5,6-dihydroindolo[1,2-a]quinoxaline 
• 1360546-63-9 7-methyl-6-phenyl-5,6-dihydroindolo[1,2-a]quinoxaline 
• 1360546-67-3 6-(4-chlorophenyl)-7-methyl-5,6-dihydroindolo[1,2-a]quinoxaline 
• 1360546-74-2 6-(4-fluorophenyl)-7-methylindolo[1,2-a]quinoxaline 
• 1360546-65-1 6-(4-fluorophenyl)-7-methyl-5,6-dihydroindolo[1,2-a]quinoxaline 
• 1360546-76-4 7-methyl-6-(p-tolyl)indolo[1,2-a]quinoxaline 

Relevant academic research and scientific papers

Synthesis of 4-Aryl Pyrrolo[1,2-α]quinoxalines via Iron-Catalyzed Oxidative Coupling from an Unactivated Methyl Arene

Herein, we describe the direct synthesis of pyrrolo[1,2-α]quinoxaline via oxidative coupling between methyl arene and 1-(2-aminophenyl) pyrroles. Oxidation of the benzylic carbon of the methyl arene was achieved by di-t-butyl peroxide in the presence of an iron catalyst, followed by conversion to an activated aldehyde in situ. Oxygen played a crucial role in the oxidation process to accelerate benzaldehyde formation. Subsequent Pictet-Spengler-type annulation completed the quinoxaline structure. The protocol tolerated various kinds of functional groups and provided 22 4-aryl pyrrolo[1,2-α]quinoxalines when various methyl arene derivatives were used. The developed method proceeded in air, and all catalysts, reagents, and solvents were easily accessible.

Palladium-catalyzed sequential acylation/annulation of indoles with acyl chlorides using primary amine as the directing group

An attractive and convenient strategy for the direct acylation/annulation of indoles has been developed using Pd(0) as an efficient catalyst. The main feature of this protocol is the use of acyl chlorides as the acylating agents with the primary amine as the directing group. A variety of indolo[1,2-a]quinoxalines were readily obtained in reasonable efficiency and satisfactory yields with good functional group tolerance. Based on control experiments, a tentative catalytic mechanism was proposed.

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

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.

N,N-Dimethylformamide as Carbon Synthons for the Synthesis ofN-Heterocycles: Pyrrolo/Indolo[1,2-a]quinoxalines and Quinazolin-4-ones

N,N-dimethylformamide (DMF) as synthetic precursors contributing especially the methyl, acyl, and amino groups has played a significant role in heterocycle syntheses and functionalization. In this protocol, a wide range of pyrrolo/indolo[1,2-a]quinoxalines and quinazolin-4-ones were obtained in moderate to good yields by using elemental iodine without any metal or peroxides. We considered thatN-methyl andN-acyl of DMF participate and complete the reaction separately through different mechanisms, which displayed potential still to be explored of DMF.

Synthesis of indolo- And pyrrolo[1,2-: a] quinoxalinones through a palladium-catalyzed oxidative carbonylation of the C 2 position of indole

A methodology that involves the Pd-catalyzed direct C(sp2)-H bond carbonylation of the C2 position of indole has been introduced for the synthesis of indolo[1,2-a]quinoxalin-6(5H)-ones. The methodology developed herein was used for the synthesis of pyrrolo[1,2-a]quinoxalin-4(5H)-ones. The reaction of N-substituted 2-(1H-indol-1-yl)anilines or 2-(1H-pyrrol-1-yl)anilines and carbon monoxide in the presence of Pd(OCOCF3)2 as a catalyst and Cu(OAc)2 as an oxidant in toluene at 80 °C forms the corresponding quinoxalinones as exclusive products in good yields. The catalytically active C-H activated intermediate Pd complex was isolated and characterized for the first time which on exposure to CO gas in toluene at 80 °C gave the corresponding quinoxalinone derivative. On the basis of isolation of the intermediate, a possible mechanism has been proposed for the C-H activated direct carbonylative annulation of 2-(5-methoxy-1H-indol-1-yl)-N,4-dimethylaniline.

Terminal methyl as a one-carbon synthon: Synthesis of quinoxaline derivatives: Via radical-type transformation

An iron-promoted method for the construction of pyrrolo[1,2-a]quinoxaline derivatives has been developed. Ferric chloride served as a promoter and as a Lewis acid in the reaction. Solvents provided the corresponding carbon sources simultaneously. The majority of solvents with terminal methyl groups, including ethers, amines and dimethyl sulfoxide, were reactive in the synthesis of quinoxaline derivatives at a certain yield via C-H(sp3) amination/C-O or C-N (C-S) cleavage. This method was applicable to a wide range of pyrrolo[1,2-a]quinoxaline and indolo[1,2-a]quinazoline substrates.

Palladium-Catalyzed Primary Amine-Directed Decarboxylative Annulation of α-Oxocarboxylic Acids: Access to Indolo[1,2-a]quinazolines

An efficient protocol for the preparation of indolo[1,2-a]quinazolines via palladium-catalyzed decarboxylative annulation of indols with α-oxocarboxylic acids has been realized by using primary amine as a directing group (DG). This transformation proceeds smoothly with exclusive regioselectivity and represents an one-pot Domino synthesis of indo-lo[1,2-a]quinazolines from α-oxocarboxylic acids. (Figure presented.).

Catalyst-Controlled Chemodivergent Annulation to Indolo/Pyrrolo-Fused Diazepine and Quinoxaline

Catalyst-controlled chemodivergent annulation between o-indolo anilines and diazo compounds has explored for the synthesis of indolo-fused diazepine and quinoxaline. Under the Rh(III) catalyst, reaction proceeded through the free amine assisted C2?H activation followed by amidation leading to the diazepino[1,7-a]indole in a highly selective manner. While with Ru(II) catalyst, reaction involves formation Ru?carbene complex followed by ?NH2 group insertion and cascade cyclization via metallo-ene type reaction, β-hydride elimination to furnish the indolo[1,2-a]quinoxaline as the predominating product. This strategy directs modular approach towards the construction of unique indolo-fused diazepine/quinoxaline as well as pyrrolo-fused diazepine/quinoxaline scaffolds in excellent yields. (Figure presented.).

Metal-Free Synthesis of Pyrrolo[1,2- a ]quinoxalines Mediated by TEMPO Oxoammonium Salts

We herein describe a novel TEMPO oxoammonium salt initiated Pictet-Spengler reaction of imines, generated in situ from carbonyl compounds and pyrrole- or indole-containing substrates, to afford 4,5-dihydropyrrolo[1,2- a ]quinoxalines or 5,6-dihydroindolo[1,2- a ]quina-oxalines in good to excellent yields. Moreover, a one-pot synthesis of a biologically important quinoxaline is achieved via a cyclization-dehydrogenation process using one equivalent of the oxoammonium salt.