Studies On The Synthesis Of Substituted Thiazole And Imidazole Compounds Under The Participation Of 2H-Azirines

2H-Azirine is a kind of ternary heterocyclic rings with two C atoms and one N atom,which was first studied by Neber et al.in the 1930s.The structure containing a C=N double bond and two single bonds,and it can show four different ways of breakage,which makes it have excellent reactivity whether to be electrophilic or nucleophilic reagent,or dienophile,bipolar reagent and so on.Result-oriented,we chose 2H-Azirines as substrate and synthesized two different nitrogenous five-membered heterocyclic derivatives—2,4,5-trisubstituted thiazoles and 1,2,4,5-tetrasubstituted imidazoles,which are widely used in the organic synthesis,drug intermediates,functional materials and other fields.Our research mainly consists of two parts:1.Catalysed by HClO₄,2,4,5-trisubstituted thiazoles have been synthesized from 2H-azirines and thioamides.The bond breaks exhibited by 2H-azirines in the protocol were usually realized by metal catalyst before.Our study will help to further develop the related chemistry.Besides,we have developed a new method for the synthesis of substituted thiazoles with good yields and extensive substrate scope.2.Through the reaction of 2H-azirines and 2-aminobenzyl alcohol,we synthesized a new structure of 1,2,4,5-tetrasubstituted imidazoles.This structure preserves the alcohol hydroxyl group from substrate,which means it has the possibility to participate in the synthesis of various organic products.Further optimization and exploration are underway.