Use of 3-Halobut-3-en-1-ol and N-(3-Halobut-3-en-1-yl)-4-Methylbenzenesulfonamide in the Prins Reaction: Access to Oxygen and Nitrogen Heterocycles

Abstract

The content of this thesis is systematically organized into five chapters, each reflecting the outcomes of the experimental investigations conducted throughout the research period. Chapter 1 provides an overview of heterocyclic compounds and their biological significance and summarizes the reported methodologies for their synthesis. Chapter 2 focuses on the diastereoselective synthesis of 2,6-disubstituted tetrahydropyranones through Prins cyclization of 3-bromobut-3-en-1-ols and aldehydes. Chapter 3 describes the stereoselective synthesis of gem-dihalopiperidines through halo-aza-Prins cyclization reaction of halogenated homoallylic amine and aldehydes. Chapter 4 presents BF3.OEt2 mediated cascade synthesis of 4H-3,1-Benzoxazines from 2-azidobenzaldehydes and homoallylic alcohols. Finally, Chapter 5 elaborates on the use of halogenated homoallylic amine for the highly diastereoselective synthesis of gem-dihalopiperidines and regioselective synthesis of 4-halo-1,2,3,6-tetrahydropyridines.