100381-43-9

Upstream product

• 108-94-1 cyclohexanone 
• 58010-91-6 4-methyl-2-p-tolylazo-aniline 
• 765-87-7 cyclohexane-1,2-dione 
• 496-72-0 4-methyl-1,2-diaminobenzene 
• 7647-01-0 hydrogenchloride 
• 578-46-1 5-methyl-2-nitroaniline 
• 120-80-9 benzene-1,2-diol 
• 931-17-9 1,2-Cyclohexanediol 
• 89-62-3 4-methyl-2-nitroaniline 

Downstream Products

• 18450-16-3 phenazine-2-carboxylic acid 

Relevant academic research and scientific papers

Direct synthesis of novel quinoxaline derivativesviapalladium-catalyzed reductive annulation of catechols and nitroarylamines

Here, a palladium-catalyzed new hydrogenative annulation reaction of catechols and nitroarylamines, allowing straightforward access to two classes of novel quinoxaline derivatives, is reported. The reaction proceeds with operational simplicity, an easily available catalyst system, and a broad substrate scope, and without the need for pre-functionalization, which offers the potential for further design of new reductive transformations of renewable resources into value-added products.

In water organic synthesis: Introducing itaconic acid as a recyclable acidic promoter for efficient and scalable synthesis of quinoxaline derivatives at room temperature

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.

NaOH-Mediated Direct Synthesis of Quinoxalines from o-Nitroanilines and Alcohols via a Hydrogen-Transfer Strategy

A NaOH-mediated sustainable synthesis of functionalized quinoxalines is disclosed via redox condensation of o-nitroamines with diols and α-hydroxy ketones. Under optimized conditions, various o-nitroamines and alcohols are well tolerated to generate the desired products in 44-99% yields without transition metals and external redox additives.

Iron-Catalyzed Hydrogen Transfer Reduction of Nitroarenes with Alcohols: Synthesis of Imines and Aza Heterocycles

A straightforward and selective reduction of nitroarenes with various alcohols was efficiently developed using an iron catalyst via a hydrogen transfer methodology. This protocol led specifically to imines in 30-91% yields, with a good functional group tolerance. Noticeably, starting from o-nitroaniline derivatives, in the presence of alcohols, benzimidazoles can be obtained in 64-72% yields when the reaction was performed with an additional oxidant, DDQ, and quinoxalines were prepared from 1,2-diols in 28-96% yields. This methodology, unprecedented at iron for imines, also provides a sustainable alternative for the preparation of quinoxalines and benzimidazoles.

Preparation method of tetrahydrophenazine derivative

The present invention discloses a preparation method of a tetrahydrophenazine derivative. The preparation method comprises the following steps: adding a nitroamine compound, a diphenol compound, a metal catalyst, an additive, a reducing agent and a solvent in a reactor, and conducting stirring and reaction to obtain a tetrahydrophenazine derivative. A structure of the nitroamine compound is shownby a general formula (1) and a structure of the diphenol compound is shown by a general formula (2); wherein R1 is independently selected from methyl, methoxy, amino, piperidyl or trifluoromethyl; R2is independently selected from methyl or ester groups; and n and m each represents an integer of 0-4. The stable and readily available nitroaniline compound and the diphenol compound derived from biomass are used as raw materials to synthesize the tetrahydrophenazine derivative in one step. The preparation method has simple synthesis steps, non-toxic raw materials, low cost and easy availability,and low catalyst usage. The synthetic method has advantages of good functional group compatibility and high atom economy, and has potential to prepare the tetrahydrophenazine derivative in one step ina large scale.

Nickel-Catalyzed Direct Synthesis of Quinoxalines from 2-Nitroanilines and Vicinal Diols: Identifying Nature of the Active Catalyst

The inexpensive and simple NiBr2/1,10-phenanthroline system-catalyzed synthesis of a series of quinoxalines from both 2-nitroanilines and 1,2-diamines is demonstrated. The reusability test for this system was performed up to the seventh cycle, which afforded good yields of the desired product without losing its reactivity significantly. Notably, during the catalytic reaction, the formation of the heterogeneous Ni-particle was observed, which was characterized by PXRD, XPS, and TEM techniques.

Efficient synthesis of quinoxalines in the ionic liquid 1-n-butylimidazolium tetrafluoroborate ([Hbim]BF4) at ambient temperature

Quinoxaline derivatives have been synthesized in excellent yields using an ionic liquid (IL) (viz., 1-n-butylimidazolium tetrafluoroborate) as a reaction medium as well as promoter from various 1,2-diketones and aryl-1,2-diamines. The process is general for the synthesis of quinoxaline derivatives from aromatic as well as aliphatic-1,2-diketones. The advantages of the present method are ambient reaction temperature, simplicity of operation, high yields of products, the recyclability of the IL, and ecofriendly nature of the reaction medium. Copyright Taylor & Francis Group, LLC.