Study On The Synthesis Of Substituted Pyrrole Compounds And ?-Allenic Aldehydes Compounds

Pyrrole and its derivatives,which exist in many compounds either alone or as a core skeleton,are important five-membered heterocyclic compounds.Most of these compounds have good biological activity and are also the focus of research in the fields of materials science and medicinal chemistry.?-allenic aldehydes are important intermediates for the synthesis of heterocyclic compounds such as furan.However,since three carbon atoms in?-allenic aldehydes form two mutually perpendicular?-orbitals,it is easy to migrate from the?,?position to the?,?position,it is difficult to synthesize them.The main researches of this thesis are to explore simple methodologies of synthesizing a series of polysubstituted pyrrole derivatives and?-allenic aldehydes derivatives with simple and easily available alkyne compounds,and lay a synthetic foundation for its application.The main research results of this thesis are as follows:Part ?:Synthesis of substituted sulfonyl pyrrole compounds using homopropargylic amines and sulfinic acidsIn this paper,tert-Butyl nitrite?TBN?promoted the oxidative cyclization reaction between homopropargylic and sulfinic acid molecules,and a method for efficiently constructing3-sulfonylpyrrole derivatives under mild conditions was provided.This reaction used a cheap and readily available acetic acid as a catalyst to realize the construction of C-N,C-S,and C-C bonds.At the same time,the reaction has the advantages of high yield,good functional group compatibility,and a wide range of substrates.Part ?:CuCl participates in the synthesis of 3,3'-bipyrrole compoundsA method for synthesizing 3,3'-bipyrrole compound was reported.The method used CuCl as a catalyst to carry out oxidation cyclization reaction with two molecules of homopropargylic amines to realize the construction of 3,3'-bipyrrole compound and derivatives.This reaction was good substrate compatibility and a high yield.Part ?:Synthesis of substituted?-allenic aldehydes catalyzed by CuCl₂This paper reported the self-rearrangement reaction of homopropargylic alcohols catalyzed by CuCl₂,and provided a method for rapidly and efficiently constructing?-allenic aldehydesderivatives under simple conditions.The reaction used Selectfluor as an oxidant to achieve aryl groups migration by rearrangement reaction of homopropargylic alcohols,and a series of?-allenic aldehydes compounds were synthesized.The reaction conditions are mild,the substrate compatibility is good,and the yield is high.