[1,2] C-C Migration Of TMS Group In Pyrroles

Pyrrole, especially poly-substituted pyrroles, are important structural unit of many natural compounds. They are not only an integral part of many compounds, but also are the materials of many kinds of heterocyclic compounds.2,4-disubstituted pyrrole and its derivatives are a class of biologically active natural compounds, which can be widely used in pharmaceutical intermediates.Since the1960s, the silicon industry is formed and expanded gradually, with the discovery and study of organosilicon compounds. Organosilicon compounds in organic molecules may show their special properties. For example, trimethylsilyl (TMS) group, is widely used in the carbon-silicon bond cleavage, because of its stabilizing effect of P-carbocations ((3effect). Therefore, the TMS groups play an very important role in the synthesis of substituted pyrroles.We carried out the studies on the rearrangement of TMS group. We synthesize3,4-bis (trimethylsilyl)-1H-pyrrole in accordance with the literature method. After that,2,4-bis (trimethylsilyl)pyrrole is synthetized by the TMS [1,2] C-C rearrangement from3,4-bis (trimethylsilyl) pyrrole. The rearrangement products are further carried out in situ iodination reaction in order to inject different groups in2,4-disubstituted pyrrole. We also optimize the reaction conditions and expand reaction substrate, so that this synthetic method have the advantage of the mild reaction conditions, the reaction high yield, etc.. Several of new compounds are synthesized and their structures are determined spectropitally. This method provide a new addition to the methodology for the synthesis of2,4-disubstituted pyrroles.