Study Of Intramolecular Multi-component Reactions Involving Tert-butylsulfoxides And Isocyanides

The classic isocyanide-based multicomponent reactions(IMCRs),named after Passerini [1,2] and Ugi [3-5](Figure 1),are particularly suitable for combinatorial chemistry.Multi-component reaction allows the introduction of sevsral diversity inputs in just one synthetic step.These practical synthetic methods are widely used in the synthesis of candidate drug libraries [6-8].The classical Passerini reaction and Ugi reaction are very suitable for exploring the diversity of substituents,and they can be used not only to generate different molecular scaffolds but also to generate heterocyclic systems.In view of the importance of heterocyclic compounds in medicinal chemistry,many efforts have recently been made to explore their synthesis[9].The intramolecular multi-component reaction provides a very effective method for obtaining heterocyclic systems.Chemists tend to be more interested in the structural features of functional groups,such as sulfenic acid,and some compounds containing these functional groups are called "transient species";however,some compounds are more stable.This feature is related to its nearby structural features and nearby functional groups.Sulfenic acid is unstable because of its good nucleophilicity and good electrophilicity.Pure sulfenic acid can react with itself to give sulfonic acid thioester.[10](Figure 2),we will discuss this issue in this article as well.All multicomponent reactions involving isocyanides are due to having a carbon atom center that is both electrophilic and nucleophilic.However,from the previous studies on Passerini reaction and Ugi reaction,most of the studies so far have found that most of the multicomponent reactions involving isocyanides all have a carbon atom as the electrophilic center.Therefore,in this field of research,it is also important to develop non-carbon atoms as electrophilic centers.This paper presents a multi-component reaction with sulfenic acid as an electrophile.It is mainly about that sulfenic acid,generated by the thermolysis,is attacked by isocyanide at the center of sulfur,and a new functional group was obtained through the isocyanide attacked by another nucleophile.The main work of this paper includes the following two aspects:First,using the new multi-component reaction to synthesize different types of heterocyclic compounds.After nucleophilic reaction between isocyanide and sulfenic acid,we can form different heterocyclic compounds by changing different nucleophilic centers,such as carbon,nitrogen and oxygen.We use this method to synthesize a series of new heterocyclic compounds.The chemical characterization(1H-NMR,13C-NMR,HR-Ms et al.)of these compounds has been obtained.Second,using the new multi-component reaction to synthesize of pharmaceutical intermediates,catalytic compounds.A series of isothiourea catalysts and pharmaceutical intermediates were synthesized by the new method.Compared with the classical synthesis method,this synthesis method is economical and pollution-free,and the operation is simple.The chemical characterization(1H-NMR,13C-NMR,HR-Ms et al.)of these compounds has been obtained.