Synthesis of Nitrogen Heterocycles from Saccharide Derivatives

Abstract

Publisher Summary This chapter discusses the formation of heterocycles that contain nitrogen and involve atoms of the original sugar, and not the combination of existing heterocycles with saccharide derivatives. The heterocycles are classified into three, five, six, and higher membered rings, and are subdivided into the different types of monocyclic heterocycle, irrespective of other rings present in the molecule. In context to formation of three-membered nitrogen heterocycles, the first saccharide derivative having an aziridine ring was prepared by treating a D-altrose derivative with sodium methoxide, and obtaining, by nitrogen participation, 4,6- O -benzylidene-2,3-dideoxy-2,3-epimino-α-D-allopyranoside. The formation of an aziridine ring is often accompanied by the production of a five-membered ring, and the thiazoline is obtained by participation through sulfur. The relative yields of the three- and five-membered ring compounds vary considerably with the type of cyclizing agent used and the nature and stereochemistry of the reacting groups. Sugar azides are considered important starting-materials for the synthesis of epimino sugars.