7248-16-0Relevant articles and documents
Green Hydrothermal Synthesis of Fluorescent 2,3-Diarylquinoxalines and Large-Scale Computational Comparison to Existing Alternatives
Amaya-García, Fabián,Caldera, Michael,Koren, Anna,Kubicek, Stefan,Menche, J?rg,Unterlass, Miriam M.
, p. 1853 - 1863 (2021/04/02)
Here, the hydrothermal synthesis (HTS) of 2,3-diarylquinoxalines from 1,2-diketones and o-phenylendiamines (o-PDAs) was achieved. The synthesis is simple, fast, and generates high yields, without requiring any organic solvents, strong acids or toxic catalysts. Reaction times down to 90 % in all cases). Moreover, it was shown that HTS has high compatibility: (i) hydrochlorides, a standard commercial form of amines, could be used directly as combined amine source and acidic catalyst, and (ii) Boc-diprotected o-PDA could be directly employed as substrate that underwent HT deprotection. A systematic large-scale computational comparison of all reported syntheses of the presented quinoxalines from the same starting compounds showed that this method is more environmentally friendly and less toxic than all existing methods and revealed generic synthetic routes for improving reaction yields. Finally, the application of the synthesized compounds as fluorescent dyes for cell staining was explored.
In water organic synthesis: Introducing itaconic acid as a recyclable acidic promoter for efficient and scalable synthesis of quinoxaline derivatives at room temperature
Tamuli, Kashyap J.,Nath, Shyamalendu,Bordoloi, Manobjyoti
supporting information, p. 983 - 1002 (2021/02/27)
Substituted quinoxaline derivatives are traditionally synthesized by co-condensation of various starting materials. Herein, we describe a novel environmentally benign in water synthetic route for the synthesis of structurally and electronically diverse ninety quinoxalines with readily available substituted o-phenylenediamine and 1,2-diketones using cheap and biodegradable itaconic acid as a mild acid promotor in 1 hours. The reaction is performed at room temperature, which proceeds through cyclo-condensation reaction followed by obtaining the aforesaid nitrogen-containing heterocyclic adducts without performing the column chromatography up to 96% total yields. The simplicity, high efficiency, and reusable of the catalyst merits this reaction condition as “green synthesis” which enables it to be useful in synthetic transformations upto gram scale level.
Microwave-Assisted Synthesis of Heterocycles from Aryldiazoacetates**
Cousin, étienne,Elumalai, Vijayaragavan,Hansen, J?rn H.,Hansen, Stephanie R.,Kristoffersen, Tone,Starck, Eliot,Wagner, Lucille J.
, p. 7069 - 7078 (2020/11/30)
Herein, we describe a rapid microwave-assisted, metal-free synthesis of substituted quinoxalinones and quinoxalines using the carbene-mediated reaction between aryldiazo esters and 1,2-diamines. The reaction can encompass a range of substituents and structural variations to afford quinoxalin-2-ones in 14–80 % yield and corresponding quinoxalines in good to excellent yields upon oxidation (67–96 %). The approach can be employed to generate symmetrical and unsymmetrical 2,3-diarylquinoxalines, bis-quinoxalines as well as novel quinoxaline-substituted diazo esters and should be a valuable addition to the heterocycle synthesis toolbox.
