Direct Nitration Of Cyclic Ketones Tertiary ?ammonium Nitrate For The Synthesis Of Ertiary ?-Nitro,?-Substituted Scaffolds Its Applications

The nitration of aliphatic C-H bonds has been a challenging topic in modern organic synthesis,especially the C(sp~3)-H nitration at ?-positions of carbonyl compounds.In this thesis,we havestudied on the nitration of C(sp~3)-H at the ?-position of the carbonyl compound.With the assistance of copper salt,a novel nitration methodology for the efficient and direct construction of ?-nitro,?-substituted skeletons with quaternary carbon centers has been developed.In this transformation cerium ammonium nitrate could be used as a ' three birdswith one stone ' reagent,i.e.nitrating reagent,single electron oxidant and Lewis acid.At the same time,ketamine,a widely used drug molecules in clinical,has been synthesized successfully utilizing the present nitration as a key step.This thesis is divided into two chapters:Chapter 1: The application of cerium ammonium nitrate as a nitrating reagent in organic synthesis is reviewed.Chapter 2: The C(sp~3)-H nitration of 2-substituted cyclic carbonyl compounds at ?-position was successfully achieved by using cerium ammonium nitrate(CAN)as nitrating reagent,single electron oxidant and Lewis acid with copper acetate as additive.The present nitration reaction features broad substrate scope,high functional group tolerance and mild reaction conditions.Ketamine,which are used asa drug molecules in clinical was synthesized efficiently.And the reaction mechanism was also studied and the possible mechanism was proposed.