Recent Developments in Direct C–H Functionalization of Quinoxalin-2(1H)-Ones via Heterogeneous Catalysis Reactions

Abstract

In recent years, Web of Science has published nearly one hundred reports per year on quinoxalin-2(1H)-ones, which have attracted great interest due to their wide applications in pharmaceutical and materials fields, especially in recyclable heterogeneous catalytic reactions for direct C–H functionalisation. This review summarises for the first time the methods and reaction mechanisms of heterogeneous catalytic reactions of quinoxalin-2(1H)-ones, including six major types of heterogeneous catalysts involved. The heterogeneous reactions of quinoxalin-2(1H)-ones are summarised by classifying different types of catalytic materials (graphitic phase carbon nitride, MOF, COF, ion exchange resin, piezoelectric materials, and microsphere catalysis). In addition, this review discusses the future development of heterogeneous catalytic reactions of quinoxalin-2(1H)-ones, including the construction of C-B/Si/P/RF/X/Se bonds by heterogeneous catalytic reactions, the enrichment of heterogeneous catalysts such as metal oxides, graphene-based composites, doped metal nanoparticles, and molecular sieve-based porous materials, asymmetric synthesis, and other areas. The aim of this review is to contribute to the development of green and sustainable heterogeneous reaction methods for quinoxalin-2(1H)-ones with applications in materials chemistry and pharmacology.

Copper-Catalyzed, Regioselective, Unsymmetrical Homocoupling of Quinoxalin-2(1H)-ones to Form C–N Homodimers

“…The quinoxalin-2­(1 H )-ones are secondary metabolites of Streptomyces . Due to their diverse physical and pharmacological properties, they are used in a wide range of synthetic, pharmaceutical, and material chemistry applications . As a result of its inherent electrophilicity at the C3 position, quinoxalin-2­(1 H )-one has been extensively studied for radical-mediated C–H functionalization .…”

“…As a result of its inherent electrophilicity at the C3 position, quinoxalin-2­(1 H )-one has been extensively studied for radical-mediated C–H functionalization . In particular, the construction of a C–N bond at its C3 position via C–H functionalization is a key fragment for bioactive substances (Figure ) Previously, we had also carried out some research on the construction of C–N bonds at the C3 position of quinoxalin-2­(1 H )-one by the use of C–H functionalization . Recently, Ghosh’s group reported that KO t Bu-promoted C3-homocoupling of quinoxalin-2­(1 H )-ones generates symmetric dimers.…”

Chemistry, Synthesis, and Structure Activity Relationship of Anticancer Quinoxalines

“…It is a low-melting solid (29-30 • C), soluble in water, and a weak base (pKa = 0.56) [15]. Several studies were performed and displayed a wide range of pharmacological activities for quinoxaline derivatives (Figure 1) [16][17][18][19][20][21][22][23][24][25][26][27][28][29][30]. Additionally, quinoxalines are used for crop protection as a component of insecticides, herbicides, and fungicides [31][32][33][34][35].…”