A Direct Method for Oxidizing Quinoxaline, Tetraazaphenanthrene, and Hexaazatriphenylene Moieties Using Hypervalent λ³-Iodinane Compounds

Abstract

An efficient oxidation reaction of various electron-poor quinoxaline-core-containing compounds, such as quinoxalines, 1,4,5,8-tetraazaphenanthrenes, and 1,4,5,8,9,12-hexaazatriphenylene, using [bis(trifluoroacetoxy)iodo]benzene is reported. These compounds are converted into the corresponding quinoxalinediones in good to high yields at room temperature using an acetonitrile/water solvent mixture. This unprecedented reaction should enable the synthesis of a wide variety of compounds useful in several fields of chemistry.

New Ruthenium‐Based Probes for Selective G‐Quadruplex Targeting

“…This synthetic route is very simple and affords pyrazine derivatives in good yields in most cases. Nevertheless, it requires two different reagents, that is, the diamine and the dione, the synthesis of which could be more problematic . Another strategy reported in the literature to form a pyrazine ring is the homocoupling of two amines, but the only example described so far proceeds through an enzymatic catalysis to afford tetrapyrido[3,2‐ a :2′,3′‐ c :3′′,2′′‐ h :2′′′,3′′′‐ j ]phenazine (tpphz); Figure b) .…”

Prodrug Approach toward the Development of a PET Radioligand for Imaging the GluN2A Subunits of the NMDA Receptor

“…Furthermore, on the basis of our previous experience, 8 we reasoned that protection of the NH functionality in the quinoxalinedione moiety would be necessary to achieve a meaningful radiochemical yield because the free NH groups would form hydrogen bonds with [ 18 F]F − and drastically lower the radiochemical yield. To address these problems, we investigated two strategies for the preparation of the masked compound [ 18 F]AFA233-prodrug (see Figure 1 Inspired by the work of Moucheron and coworkers 9 on the oxidation of quinoxalines to quinoxalinediones with hypervalent λ 3 -iodine reagents ([bis(trifluoroacetoxy)-iodo]benzene or (diacetoxyiodo)benzene), we evaluated this protocol for the oxidation of model compound 2 to the corresponding quinoxalinedione 1. Unfortunately, the conversion to the desired compound 1 was rather low (∼7%).…”

“…Inspired by the work of Moucheron and coworkers on the oxidation of quinoxalines to quinoxalinediones with hypervalent λ 3 -iodine reagents ([bis­(trifluoroacetoxy)-iodo]­benzene or (diacetoxyiodo)­benzene), we evaluated this protocol for the oxidation of model compound 2 to the corresponding quinoxalinedione 1 . Unfortunately, the conversion to the desired compound 1 was rather low (∼7%).…”

A theoretical study on diastereoselective oxidative dearomatization by iodoxybenzoic acid

“…Hypervalent iodine reagents [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17] have become tools of choice for performing oxidation during organic synthesis. Among these reagents, 2-iodoxybenzoic acid (IBX) has found widespread use in organic synthesis, mainly due to its ready accessibility, mild reactivity, and the possibility of modifying it into variants that can be used in aqueous solutions [18,19].…”