33488-35-6

Upstream product

• 1603-79-8 phenylglyoxylic acid ethyl ester 
• 95-83-0 4-Chloro-1,2-phenylenediamine 
• 62-53-3 aniline 
• 2427-71-6 6-chloro-1,2-dihydroquinoxalin-2-one 
• 369-57-3 benzenediazonium tetrafluoroborate 
• 536-74-3 phenylacetylene 
• 424799-86-0 4-chloro-2-nitro-N-(2-phenylethen-1-yl)benzenamine 

Downstream Products

• 76672-25-8 2,6-Dichloro-3-phenylquinoxaline 

Relevant academic research and scientific papers

Aqueous hydrofluoric acid catalyzed facile synthesis of 2,3,6-substituted quinoxalines

A versatile synthetic route for the preparation of 2,3,6-trisubstituted quinoxalines in excellent yield is developed from θ-diamines and 1,2-dicarbonyl compounds in which aqueous hydrofluoric acid was employed as the medium and catalyst. Other salient features of this protocol include milder conditions, absence of coupling agents, and easy workup procedures.

Electrochemical Cross-Coupling of C(sp2)?H with Aryldiazonium Salts via a Paired Electrolysis: an Alternative to Visible Light Photoredox-Based Approach

Photoredox-based C?H bond functionalization constitutes one of the most powerful and atom-economical approaches to organic syntheses. During this type of reaction, single electron transfer takes place between the photocatalyst (PC) and redox- active substrates. Electrosynthesis also involves electron transfer between substrates and electrodes. In this paper, we focus upon electrochemical cross-coupling of C(sp2)?H with aryldiazonium salts and have developed an efficient electrochemical approach to the Minisci-type arylation reaction. The constant current paired electrosynthesis proceeds in a simple undivided cell without external supporting electrolyte, features a wide range of substrates and is easy to scale-up. These results demonstrate that photoredox-based cross-coupling of C(sp2)?H with aryldiazonium salts can also proceed successfully under paired electrolysis conditions, thereby contributing to understanding of the parallels between photosynthesis and electrosynthesis. (Figure presented.).

Visible-light-induced, copper(i)-catalysed C-N coupling between o-phenylenediamine and terminal alkynes: One-pot synthesis of 3-phenyl-2-hydroxy-quinoxalines

Visible-light-initiated aerobic direct C-N coupling between o-phenylenediamines and terminal acetylenes was performed using simple copper(i) chloride as a catalyst for the synthesis of quinoxaline derivatives. The current method works well for a wide range of electron rich as well as electron poor group-substituted o-phenylenediamines and phenylacetylenes. The key component in the reaction is the direct photo-excitation of in situ generated copper arylacetylide (λabs = 420-480 nm). Moreover, as compared to the literature reports (thermal process), the current photochemical method is simple, mild, high yielding, and more viable towards the construction of biologically important quinoxaline derivatives from easily accessible raw materials, without the need of ligands and strong oxidants.

A novel palladium-catalyzed synthesis of 1,2-dihydroquinoxalines and 3,4-dihydroquinoxalinones.

Reactions of enamines, derived from 2-nitroanilines and alpha-substituted aldehydes, with carbon monoxide (6 atm) in the presence of a catalytic amount of bis(dibenzylideneacetone)palladium(0) (Pd(dba)(2)) and 1,3-bis(diphenylphosphino)propane (dppp) affo