209974-60-7

Upstream product

• 6025-60-1 2-(1H-pyrrol-1-yl)aniline 
• 109-94-4 formic acid ethyl ester 
• 615-43-0 2-iodophenylamine 
• 2258-42-6 formyl acetic anhydride 

Downstream Products

• 350829-07-1 1-[2-isocyanophenyl]-1H-pyrrole 
• 37046-17-6 pyrrolo[1,2-a]quinoxaline-4(5H)-thione 
• 33265-71-3 1-(2-isocyanophenyl)-1H-pyrrole 
• 234-95-7 pyrrolo[1,2-a]quinoxaline 
• 79323-12-9 4-benzoylpyrrolo<1,2-a>quinoxaline 

Relevant academic research and scientific papers

Synthesis of pyrrolo[1,2-a]quinoxaline derivatives by lewis acid-catalyzed reactions of 1-(2-isocyanophenyl)pyrroles

1-(2-Isocyanophenyl)pyrroles have been prepared. They react in moderate to good isolated yields with aldehydes (or ketones), oxiranes, and acetals in the presence of catalytic amounts of diethyl ether-boron trifluoride to give pyrrolo [1,2-a]quinoxalines carrying an oxyalkyl substituent, such as α-hydroxyalkyl, β-hydroxyalkyl, or α-alkoxyalkyl, at the 4-position.

Synthesis of pyrrolo[1,2-a]quinoxaline and its 4-(1-hydroxyalkyl) derivatives by Lewis acid-catalyzed reactions of 1-(2-isocyanophenyl)pyrrole

When 1-(2-isocyanophenyl)pyrrole was treated with a catalytic amount of boron trifluoride, pyrrolo[1,2-a]quinoxaline was obtained almost quantitatively. The reaction in the presence of aldehydes or ketones gave the corresponding 4-(1-hydroxyalkyl)pyrrolo[1,2-a]quinoxalines in moderate to good isolated yields.

Catalyst-free synthesis of phenanthridinesviaelectrochemical coupling of 2-isocyanobiphenyls and amines

Catalyst free synthesis of 6-aryl phenanthridines and amides through an electrochemical reaction is reported in this study. The coupling reaction proceeds by the cathodic reduction ofin situformed diazonium ions, which are formed from anilines and an alkyl nitrite. The generated aryl radical diazonium ions coupled from isocyanides furnished the desired products in good yields. This cascade reaction was conducted in an undivided cell equipped with an RVC as the anode and Pt as the cathode usingnBu4NBF4as the electrolyte at room temperature. A series of detailed mechanistic studies have also been performed, including a radical clock experiment and cyclic voltammetry analysis.

Visible-Light-Driven Difluoromethylation of Isocyanides with S-(Difluoromethyl)diarylsulfonium Salt: Access to a Wide Variety of Difluoromethylated Phenanthridines and Isoquinolines

A highly efficient approach of visible-light-driven radical difluoromethylation of isocyanides to access a wide variety of difluoromethylated phenanthridines and isoquinolines is herein described. Electrophilic S-(difluoromethyl)diarylsulfonium salt proved to be a good difluoromethyl radical precursor under photoredox catalysis. A broad range of isocyanides were tolerated to furnish the corresponding difluoromethylated phenanthridines, isoquinolines, furo[3,2-c]pyridine, and pyrido[3,4-b]indole in moderate to excellent yields under mild conditions. A plausible mechanism was also proposed.

6π-Electrocyclization in water: microwave-assisted synthesis of polyheterocyclic-fused quinoline-2-thiones

Microwave-assisted synthesis of polyheterocyclic-fused quinoline-2-thiones through the annulation of ortho-heteroaryl anilines and CS2 was realized in water without using any catalysts and additives. The desired products were obtained in high yields throu

Halogen-Bond-Promoted Photoactivation of Perfluoroalkyl Iodides: A Photochemical Protocol for Perfluoroalkylation Reactions

A new protocol for photochemical perfluoroalkylation reactions using perfluoroalkyl iodide, amine additive, and THF solvent is reported. This protocol does not require a photoredox catalyst and proceeds at ambient temperature with irradiation from a compact fluorescent lamp, low-intensity UV lamp, or sunlight. This protocol can be applied to the synthesis of perfluoroalkyl-substituted phenanthridines as well as effect the iodo-perfluoroalkylation of alkenes/alkynes and the C-H perfluoroalkylation of electron-rich arenes and heteroarenes. This C-H perfluoroalkylation reaction offers a unique method for site-selective labeling of oligopeptides at the tryptophan residue.

AgI-Promoted Difluoromethylation of Isocyanides To Give Difluoromethylated Phenanthridines

An AgI-mediated ethoxycarbonyldifluoromethylation of isocyanides has been developed. This radical cascade reaction involves the addition of difluoromethylene radical to the isocyanide functionality, and subsequent homolytic aromatic substitution to give difluoromethylated phenanthridines with a good functional-group tolerance.

Synthesis of highly functionalized polycyclic quinoxaline derivatives using visible-light photoredox catalysis

A mild and facile method for preparing highly functionalized pyrrolo[1,2-a]quinoxalines and other nitrogenrich heterocycles, each containing a quinoxaline core or an analogue thereof, has been developed. The novel method features a visible-light-induced decarboxylative radical coupling of ortho-substituted arylisocyanides and radicals generated from phenyliodine(III) dicarboxylate reagents and exhibits excellent functional group compatibility. A wide range of quinoxaline heterocycles have been prepared. Finally, a telescoped preparation of these polycyclic compounds by integration of the in-line isocyanide formation and photochemical cyclization has been established in a three-step continuousflow system.

Synthesis of 4-(1-dialkylaminoalkyl)pyrrolo[1,2-a]quinoxalines

The reaction of 1-(2-isocyanophenyl)pyrroles (1), which were readily prepared from commercially available or known 1-(2-aminophenyl)pyrroles by formylation in refluxing ethyl formate followed by dehydration with POCl3/Et3N in THF, wi