Iodine-Promoted Thioylation and Dicarbonylation of Enaminone α-C Sites: Synthesis of Fully Substituted Thiazoles via C═C Bond Cleavage

Abstract

A novel iodine-promoted difunctionalization of α-C sites in enaminones was demonstrated as a means of synthesizing a variety of fully substituted thiazoles by constructing C−C(CO), C−S, and C−N bonds. This transformation allows the realization of enaminones as unusual aryl C2 synthons and simultaneously allows the thioylation and dicarbonylation of α-C sites. A preliminary mechanistic study was performed and indicated that the cleavage of C�C bonds in enaminones involves a bicyclization/ring-opening and oxidative coupling sequence.

N-Benzylhydroxylamine as a novel synthetic block in “C1N1” embedding reaction via α-C(sp3)–H activation strategy

“…Toward this goal and based on our previous work on heterocyclic synthesis, 9 we envisaged that the phenylglyoxal generated in situ by aryl methyl ketones could be captured by N -benzylhydroxylamine hydrochlorides to yield the novel acyl ketonitrone intermediates A . Subsequently, the carbonyl group of intermediates A could be trapped by arylamines.…”