Iodine-Promoted Oxidative Cyclization of Methyl Azaarenes and α-Amino Ketones for One-Pot Synthesis of 2-Azaaryl-5-aryl Oxazoles

Abstract

A high efficiency protocol was developed for the synthesis of 2,5-disubstituted oxazoles via iodine-promoted oxidative domino cyclization. These reactions were performed with readily available methyl azaarenes and α-amino ketones under metal-free conditions. This protocol is a simple method with high functional group compatibility, a wide range of substrates, and excellent yield, providing a new way to synthesize azaarene-attached oxazoles.

Oxytrofalcatin Puzzle: Total Synthesis and Structural Revision of Oxytrofalcatins B and C

“…In this biosynthetic pathway, we can consider another pathway (Scheme B). If the dehydrative cyclization of 10–11 occurs via path b, the corresponding oxazoline 26 is formed . This oxazoline would subsequently be aromatized to give 2,5-diaryloxazole 27 …”

Recent advances in iodine–DMSO mediated C(sp3)–H functionalization of methyl-azaarenes via Kornblum oxidation

“…In 2022 Zhu and coworkers 44 reported a method for the synthesis of substituted oxazoles 116 (Scheme 26). A reaction of methylazaarenes and aminoketones 115 in the presence of 1.5 equivalents of iodine and 0.5 equivalents of TsOH·H 2 O in DMSO provided the desired products 116 in 40–86% yields.…”