33265-65-5

Upstream product

• 6025-60-1 2-(1H-pyrrol-1-yl)aniline 
• 100-52-7 benzaldehyde 
• 33265-60-0 1-(2-nitrophenyl)-1H-pyrrole 
• 492-70-6 1,2-diphenyl-1,2-ethanediol 
• 88-74-4 2-nitro-aniline 
• 3389-01-3 4-phenylpyrrolo[1,2-a]quinoxaline 
• 94-02-0 ethyl 3-oxo-3-phenylpropionate 
• 100-51-6 benzyl alcohol 

Downstream Products

• 1610926-48-1 2,6-dimethyl-N-((4-phenylpyrrolo[1,2-a]quinoxalin-5(4H)-yl)methylene)aniline 
• 3389-01-3 4-phenylpyrrolo[1,2-a]quinoxaline 
• 1172101-42-6 C₂₆H₂₈ClN₃O₂ 

Relevant academic research and scientific papers

Structural Basis of Sirtuin 6 Activation by Synthetic Small Molecules

Sirtuins are protein deacylases regulating metabolism and stress responses, and are implicated in aging-related diseases. Small molecule activators for the human sirtuins Sirt1-7 are sought as chemical tools and potential therapeutics, such as for cancer.

Direct Synthesis of Pyrrolo[1,2-α]quinoxalines via Iron-Catalyzed Transfer Hydrogenation between 1-(2-Nitrophenyl)pyrroles and Alcohols

Herein, we describe novel iron-catalyzed transfer hydrogenation between alcohols and 1-(2-nitrophenyl)pyrroles for the synthesis of pyrrolo[1,2-α]quinoxalines. The tricarbonyl (η4-cyclopentadienone) iron complex catalyzed the oxidation of alcohols and the reduction of nitroarenes, and the corresponding aldehydes and aniline were generated in situ. The resulting Pictet-Spengler-type annulation/oxidation completed the quinoxaline structure formation. The protocol tolerated various kinds of functional groups and provided 29 samples of 4-substituted pyrrolo[1,2-α]quinoxalines. The developed method was also applied for the synthesis of additional polyheterocycles.

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.

Highly Stereoselective Metal-Free Hydrogenations of Pyrrolo[1,2- a]quinoxalines

A metal-free hydrogenation of pyrrolo[1,2-a]quinoxalines has been successfully realized by using the combination of B(C6F5)3 and tris(4-methoxyphenyl)phosphine to furnish the corresponding 1,2,3,3a,4,5-hexahydropyrrolo[1,2-a]quinoxalines in 59-99% yields. For 4-aryl-substituted pyrrolo[1,2-a]quinoxalines, high cis selectivities were obtained, but trans-selectivities were achieved for the 4-methyl-substituted substrates.

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.

Molybdenum-catalyzed synthesis of nitrogenated polyheterocycles from nitroarenes and glycols with reuse of waste reduction byproduct

A novel domino reduction/imine formation/intramolecular cyclization/oxidation for the efficient synthesis of pyrrolo(indolo)[1,2-a]quinoxalines and pyrrolo(indolo)-[3,2-c]-quinolines from readily available nitrobenzenes and glycols is reported. The process utilizes the carbonyl byproduct of the initial dioxomolybdenum(VI)-catalyzed reduction of nitroaromatics with glycols as a reagent for the imine generation. This method represents the first sustainable domino reaction for the preparation of biologically relevant heterocycles that internally incorporates the waste formed in the first step to the final product.

An eco-friendly Pictet-Spengler approach to pyrrolo- and indolo[1,2-a]quinoxalines using p-dodecylbenzenesulfonic acid as an efficient Br?nsted acid catalyst

A facile and environmentally benign Pictet-Spengler strategy for the synthesis of a series of biologically important pyrrolo- and indolo[1,2-a]quinoxalines has been developed by reacting 1-(2-aminophenyl)-pyrrole or 1-(2-aminophenyl)indoles with a wide range of aromatic aldehydes, acetophenones or isatins in ethanol at ambient temperature using p-dodecylbenzenesulfonic acid (p-DBSA) as an efficient Br?nsted acid-surfactant combined catalyst. This methodology was found to be applicable to generate diverse quinoxaline derivatives in fairly good yields under mild reaction conditions.

Exploiting the divalent nature of isonitriles: A novel Pictet-Spengler amidination process

An isocyanide-based multicomponent reaction (IMCR) utilized for the rapid assembly of novel, biologically relevant dihydropyrrolo[1,2-a]quinoxalines- amidines is herein presented. Starting from 1-(2-aminophenyl)pyrroles, aldehydes, and isonitriles, the ta

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.

Hit-to-lead optimization of pyrrolo[1,2-a]quinoxalines as novel cannabinoid type 1 receptor antagonists

Hit-to-lead optimization of a novel series of N-alkyl-N-[2-oxo-2-(4-aryl-4H-pyrrolo[1,2-a]quinoxaline-5-yl)-ethyl]-car boxylic acid amides, derived from a high throughput screening (HTS) hit, are described. Subsequent optimization led to identification of