Studies On The Reactions And Applications Of N-Acylbenzotriazoles

The dissertation consists of three chapters. In the first one, the organic reactions and applications of benzotriazole derivatives are briefly described. The second one is focused on the acylation reaction with saturated N-acylbenzotriazoles. The third chapter discusses the selective 1,2- and 1,4-addition of α,β-unsaturated acylbenzotriazoles with nucleophilic reagents.Chapter one is a brief review on two types of benzotriazole derivatives, namely, N-acylbenzotriazoles and α-heteroatom alkylbenzotriazoles (N-benzotriazolyl group and a heteroatom are attached to a same carbon atom). The methods for their synthesis and the application of them in organic transformation are discussed.In chapter two, firstly, the acylation reaction of hydrazines or aqueous hydrazine with saturated N-Acylbenzotriazoles was studied. It was found that under very mild conditions three types of acylhydrazines in moderate to excellent yields could be synthesized. Subsequent study was focused on the substitution of acyl with N-acylbenzotriazoles for acetyl in ethyl acetoacetate, methyl acetoacetate and acetylacetone. Catalyzed by Lewis acid samarium triiodide (SmI₃), the acyl exchange reaction proceeded smoothly to afford the corresponding β-ksto esters and β-diketones. The operational simplicity and good efficiency make the reaction a facile synthesis of β-keto esters and β-diketones.Chapter three focuses on the selective 1,2- and 1,4-addition of α,β-unsaturated acylbenzotriazoles with a variety of nucleophiles. When treated with samarium thiolates, the 1, 2-addition predominated and good to...