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

Abstract

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.

Description

technical field [0001] The invention belongs to the field of organic synthetic chemistry, in particular to a photocatalytic preparation method of a 3-aminoquinoxalin-2(1H)-one compound Background technique [0002] 3-Aminoquinoxaline-2(1H)-one compounds have a wide range of applications in the fields of organic synthesis and medicinal chemistry. Its skeleton derivatives widely exist in a variety of biologically active drug molecules, and they have significant biological activities such as anti-tumor, anti-cancer, antibacterial, hypotensive, and anti-diabetic. In recent years, various 3-aminoquinoxaline-2 (1H)-ketone compounds have also been developed as clinical therapeutic drugs, as shown in the following structural formula, compound A is used as a calcium ion channel blocker; compound B Used as an aldose reductase reductase inhibitor; Compound C is a PAS kinase regulator; Compound D is a histamine-4 receptor antagonist (WO 2009045382A1; Chem. Abstr. 2009,150, 398369; Eur...

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Problems solved by technology

Although this method is more effective, there are still some shortcomings in this type of reaction. For example, as shown in the following reaction formula, route (a) needs to add 2 equivalents of potassium permanganate metal reagent or 1.2 equivalents of AgPy2MnO4 as the oxidant, and the reaction Poor functional group compatibility, serious environmental pollution (Tetrahedron 2008, 64, 696−707); route (b) uses transition metal copper salt to catalyze the reaction, and the reaction requires high reaction temperature, and the problem of metal ion residue is difficult to deal with (Org. Biomol. Chem. 2016, 14, 8428−8432 ;Catal Commun 2017, 101, 20-25); route (c) requires molecular iodine as a catalyst and 2 equivalents of tert-butanol peroxide as an oxidant, and the use of equivalent peroxy compounds is potentially dangerous when the reaction is scaled up (J. Org . Chem. 2017, 82, 4784−4792); in summary, most of the current synthesis methods of 3-aminoquinoxalin-2(1H)-one have obvious limitations such as the need to use highly polluting metal strong oxidizing reagents , or metal catalysts, or equivalent peroxide oxidants, which seriously pollute the environment

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