32464-46-3

Upstream product

• 83-34-1 3-Methylindole 
• 1045601-63-5 3-methyl-1-(2-nitro-phenyl)-1H-indole 
• 870072-59-6 3-methyl-1-(2-aminophenyl)-1H-indole 
• 100-52-7 benzaldehyde 
• 1360546-63-9 7-methyl-6-phenyl-5,6-dihydroindolo[1,2-a]quinoxaline 
• 103-82-2 phenylacetic acid 
• 108-88-3 toluene 
• 98-88-4 benzoyl chloride 
• 615-43-0 2-iodophenylamine 
• 611-73-4 Benzoylformic acid 
• 88-74-4 2-nitro-aniline 
• 94-02-0 ethyl 3-oxo-3-phenylpropionate 
• 120-46-7 1,3-diphenylpropanedione 

Relevant academic research and scientific papers

Elemental Sulfur Mediated Synthesis of Pyrrolo[1,2- a ]quinoxalines from 1-(2-Nitroaryl)pyrroles

Methods to afford pyrrolo[1,2- a ]quinoxalines often require the use of prefunctionalized aniline precursors, transition metals, and/or harsh conditions. Herein we describe a simple coupling of 1-(2-nitroaryl)pyrroles and arylacetic acids, in the presence of elemental sulfur, to furnish the fused heterocycles in good yields. The conditions are compatible with many functionalities including ester, nitrile, halogen, and nitro groups. Use of benzyl alcohols and picoline coupling reagents was also attempted.

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.

Novel method for synthesizing indolo[1,2-a]quinoxaline derivative

The invention discloses a novel method for synthesizing an indolo[1,2-a]quinoxaline derivative. The novel synthesis method comprises the following steps: adding a palladium catalyst, an indole compound, acyl chloride, an additive, alkali and a solvent into a glass reaction container, carrying out a reaction under stirring at 110-130 DEG C under the protection of argon, and separating and purifyinga crude reaction product so as to obtain an indolo[1,2-a]quinoxaline compound. According to the invention, a coupling reaction of primary amine-guided acyl chloride and an indole derivative is developed; a series of functionalized indolo[1,2-a]quinoxaline derivatives can be constructed through simple operation; and high step economy and atom economy are achieved. In addition, the reaction in thenovel method provided by the invention has the main advantages of simple and easily-available substrate, single selectivity, good functional group tolerance and high yield.

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.).

Method for primary amine guiding construction of 7-methyl-6-phenylindolo[1,2-a]quinoxaline

The invention discloses a method for primary amine guiding construction of 7-methyl-6-phenylindolo[1,2-a]quinoxaline. In a reaction test tube, 2-(3-methyl-1H-indol-1-yl)aniline and benzoyl formic acidare added as raw materials, and after an acylation/cycl

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.

Efficient synthesis of pyrrolo[1,2-: A] quinoxalines catalyzed by a Br?nsted acid through cleavage of C-C bonds

An efficient and convenient one-pot domino reaction for the direct synthesis of pyrrolo[1,2-a]quinoxalines has been developed. This approach utilizes an imine formation reaction, SEAr reaction and cleavage of C-C bonds catalyzed by a Br?nsted acid. β-Diketones and β-keto esters are both well tolerated to give the corresponding products in moderate to excellent yields.

Lewis acid-catalyzed selective synthesis of diversely substituted indolo-and pyrrolo[1,2-a]quinoxalines and quinoxalinones by modified pictet-spengler reaction

An efficient tandem process for the selective synthesis of 1,2-annulated α-fused quinoxalines using benzotriazole methodology by a modified Pictet-Spengler reaction is described. The approach involves the reaction of arylamines 4 with aromatic aldehydes 5 to furnish 6-endo-dig-cyclized products. Dihydroquinoxalines 6 were selectively obtained by using AlCl3 in tetrahydrofuran (THF) at room temperature for two hours. However, after ten hours, quinoxalines 7 were obtained exclusively in excellent yields. A series of biologically important fluoro-and piperazenyl-substituted quinoxalines were also synthesized. This developed methodology also provides access to a novel tandem synthesis of quinoxalinones 9.