The Potential Application Of Binucleophile For Construction Of Heterocyclic Compounds And C-C Bond

Binucleophile reagent has important application in organic synthesis. In the process of the construction of some organic heterocyclic compounds, binucleophile reagent has attracted more and more attention. Benzo[d]imidazo[2,1-b]thiazole heterocyclic compounds is a kind of important organic heterocyclic compounds claiming a variety of biological activity. The reported examples of the biological activity proved the importance of this kind of heterocyclic derivatives. And looking for concise and efficient synthetic methods also becomes important topic. In the exploration of binucleophile reagent, we found an effective synthetic method to obtain benzo[d]imidazo[2,1-b]thiazole heterocyclic compounds which takes2-mercapto benzoimidazole as starting material, reacting with benzene ring contains double leaving group via SNAr reaction to get target compounds, and we also discuss the effects of different substituent.In follow-up exploration of binucleophile reagent, we found another application of this kind of reagents-C-C bond construction, in order to synthesize ketone of a-arylation. Ketone a-arylation compound in existing report mainly accomplished by transition metal catalyzed coupling reaction, transition metal can be Pd, Cu, Ni, etc. Our synthetic methods mainly take2-hydroxy acetophenone as raw materials, and react with a series of electron-insufficient benzene substrate via Smiles rearrangement reaction, get the corresponding ketones a-arylation product.