Synthesis Of N-Substituted Pyrrole (Indole) Derivatives And Subsequent Oxidative Coupling Reactions

Based on the 1,3-dipolar cycloaddition reaction,series of N-substituted pyrrole and Nsubstituted indole derivatives were obtained.Starting from these substrates,a serial of methylene-?-butyrolactam derivative were synthesized successively.A novel tandem reaction of trans-4-hydroxy-L-proline or porphyrin-2-carboxylic acid with 2,2'-oxydibenzaldehyde derivatives has been developed.The reaction undergoes[3+2]cycloadditions and ring-opening aromatization cascade processes;with advantages such as readily available raw materials,short reaction times,high yields,and no additional catalyst or addictive.Seventeen unreported compounds with 10,11-dihydrodibenzo[b,f]oxazacyclo scaffold have been synthesized efficiently by this method.Furthermore,twelve new unsaturated ?-butyrolactams have been synthesized through single-electron free radical oxidation using N-substituted pyrrole and ?-ketoester or ?-diester as substrates while manganese acetate as an oxidant.The y-butyrolactam from ?-keto ester is a mixture of syn-anti configuration,with the ratio of syn-anti is about 1:1.