2725-16-8

Usage

InChI:InChI=1/C12H13N3O2/c16-12-11(15-5-7-17-8-6-15)13-9-3-1-2-4-10(9)14-12/h1-4H,5-8H2,(H,14,16)

Upstream product

• 110-91-8 morpholine 
• 1196-57-2 quinoxalin-2⁽¹⁾-one 
• 59564-59-9 1,2,3,4-tetrahydroquinoxalin-2-one 

Relevant academic research and scientific papers

Transition-Metal and Solvent-Free Oxidative C-H Fluoroalkoxylation of Quinoxalinones with Fluoroalkyl Alcohols

The first example of oxidative C-H fluoroalkoxylation of quinoxalinones with fluoroalkyl alcohols under transition-metal and solvent-free conditions is described. This approach provides the synthesis of fluoroalkoxylated quinoxaline derivatives with good to excellent yields under mild reactions conditions. This method can also be extended to the facile and efficient synthesis of histamine-4 receptor.

Direct oxidative C–H amination of quinoxalinones under copper-organic framework catalysis

A copper-organic framework Cu-CPO-27 was synthesized, and utilized as a recyclable heterogeneous catalyst for the direct C–H amination of quinoxalin-2(1H)-ones with amines to produce 3-aminoquinoxalin-2(1H)-ones. High yields were achieved in the presence of molecular oxygen as the oxidant. This framework was more catalytically active than a number of MOF-based catalysts. The Cu-CPO-27 also displayed higher performance than CuFe2O4 nanoparticles. The copper-organic framework catalyst could be reutilized in the synthesis of 3-aminoquinoxalin-2(1H)-ones via the direct C–H amination reaction without a remarkable deterioration in catalytic performance. To our best knowledge, this is the first heterogeneous catalytic protocol to generate 3-aminoquinoxalin-2(1H)-ones.

Metal-Free C(sp2)-H/N-H Cross-Dehydrogenative Coupling of Quinoxalinones with Aliphatic Amines under Visible-Light Photoredox Catalysis

A novel and efficient visible-light-induced C(sp2)-H/N-H cross-dehydrogenative coupling (CDC)-amination with both primary and secondary aliphatic amines at room temperature in air is developed. This photocatalytic reaction allows the direct formation of 3-aminoquinoxalin-2(1H)-ones via CDC-amination in the absence of any external oxidant added from outside. Preliminary mechanistic studies reveal that the present reaction proceeds through a radical process.

Electrochemical Dehydrogenative Cross-Coupling of Quinoxalin-2(1H)-ones with Amines for the Synthesis of 3-Aminoquinoxalinones

An efficient protocol for the synthesis of 3-aminoquinoxalinones via the electrochemical dehydrogenative C-3 amination of quinoxalin-2(1H)-ones was developed. With aliphatic amines and azoles as the nitrogen sources, a series of 3-aminoquinoxalinones was

Copper-catalysed oxidative amination of quinoxalin-2(1: H)-ones with aliphatic amines

A novel, efficient and practical method for copper-catalysed oxidative C-3 amination of quinoxalin-2(1H)-ones with primary or secondary amines as the nitrogen sources has been developed. A wide variety of 3-aminoquinoxalin-2(1H)-ones were prepared in up to 98% yield with good functional group tolerance for 24 examples. This synthetic strategy features atom economy, concise steps, easy operation, and mild reaction conditions.

Copper catalyzed aerobic oxidative amination of 3,4-dihydroquinoxalin-2(1H)-ones

A copper catalyzed aerobic sp3 C[sbnd]H amination of 3,4-dihydroquinoxalin-2(1H)-ones is developed. This protocol provides a concise method to access 3-aminoquinoxalinone derivatives with good functional-group tolerances, utilizing primary and secondary aliphatic amines as nitrogen sources under mild and simple reaction conditions. It provides a practical approach to the synthesis of pharmaceutical active 3-aminoquinoxalinones.

Photocatalytic preparation method of 3-aminoquinoxaline-2(1H)-ketone compound

The invention relates to a photocatalytic preparation method of a 3-aminoquinoxaline-2(1H)-ketone compound, in particular to a method for preparing a 3-aminoquinoxaline-2(1H)-ketone compound based onphotocatalysis. The reaction formula of the preparation method is as shown in the description, wherein R1 is a hydrogen atom or randomly substituted fluorine, chlorine, bromine, iodine, nitryl, estergroup, cyanogroup, alkoxy, aryl, heteroaryl and 1-12 carbon alkyl; R2 is randomly substituted 1-12 carbon alkyl, allyl, propargyl, aryl or hydrogen atom; R3 is randomly substituted 1-12 carbon alkyl,naphthenic base, benzyl, allyl and propargyl; and R4 is randomly substituted 1-12 carbon alkyl, allyl, benzyl, propargyl or hydrogen atom. The photocatalytic preparation method of the 3-aminoquinoxaline-2(1H)-ketone compound adopts a visible light catalytic technology, is mild in reaction condition, simple to operate, clean in energy source and safe and reliable in process; and the use of a metalreagent and a strong oxidant is avoided, and a strong application value is achieved.

A 3 - amino quinoxaline - 2 (1 H) - ketone compounds

The invention discloses a synthetic method for 3-aminoquinoxaline-2(1H)-ketone compound. A quinoxaline-2(1H)-one derivative, organic amine, and copper acetate are dissolved to dimethyl sulfoxide for reaction for 10 to 25 h at a temperature of 95 to 110 DEG C under a natural ambient condition, and the 3-aminoquinoxaline-2(1H)-ketone compound is obtained through separation and purification. A molar ratio between the quinoxaline-2(1H)-one derivative, organic amine, and copper acetate is 0.9-1.2:2.8-3.3:0.03-0.06. Each millimole quinoxaline-2(1H)-one derivative needs 2-3 mL dimethyl sulfoxide solution. The foregoing quinoxaline-2(1H)-one derivative has a general molecular formula as shown in the specification, wherein R1 is hydrogen, alkyl, aryl, halogen, or alkoxy, and R2 is hydrogen, benzyl, alkyl, or ester base. Raw materials used in the method of the invention is easy to get and gentle in reaction condition. It is unnecessary to add additional additives, a catalytic dosage is small, and a yield is high. A substrate range is wide, reaction specificity is strong, and processing is convenient and environmental friendly.

Iodine-Catalyzed C-N Bond Formation: Synthesis of 3-Aminoquinoxalinones under Ambient Conditions

A metal-free cross-dehydrogenative coupling between quinoxalinones (sp2 C-H) and amines (N-H) in the presence of catalytic iodine is reported. The reaction yields 3-aminoquinoxalinones in moderate to high yields under ambient conditions in dioxane as solvent and aqueous tert-butyl hydroperoxide (TBHP) as the terminal oxidant. The reaction is highly versatile and exhibits good functional group tolerance with a range of primary and secondary amines. It provides a practical access to pharmaceutically active 3-aminoquinoxalinone derivatives. Preliminary mechanistic studies reveal in situ iodination of the amine as the putative mode of activation.