Study On The Synthesis Of Sprio Indole Ketones And 3,7-Dioxabicyclo[4.1.0]heptan-2-imines

This thesis is divided into the following two parts: 1.The synthesis of spiroindole ketones;2.The synthesis of 3,7-dioxabicyclo[4.1.0]heptan-2-imines.1.The synthesis of spiroindole ketonesSpiroindole ketone unit is important heterocycle,exist in many natural products and pharmaceutical intermediates.A literature review indicated that,according to the construction order of the ring in the structure,these synthetic methods can be roughly divided into two types:(1)A derivatization of functionalized indole ketones under the alkaline conditions;(2)A transition metal-catalyzed intramolecular cyclization of aromatic derivatives.At present,the second method is the most used one.to get these compounds.However,it will inevitably lead to heavy metal pollution,which is harmful to the environment.Therefore,development an efficient method for the synthesis of this type of compounds remains very valuable in theory and practice.In this paper,a high-valent iodine reagent bis(tert-butylcarbonyloxy)iodobenzene [PhI(OPiv)2] is used as oxidant,a new method for the synthesis of spiroindolones from N,1-diphenylcyclopropane-1-formamides is discussed.The method has the characteristics of easy to obtain raw materials,no metal participation,easy handling and so on.2.The synthesis of 3,7-dioxabicyclo[4.1.0]heptan-2-iminesTBHP,known as t-butyl peroxide,is widely used in organic synthesis reaction because of high oxidation,no pollution to the environment.This section discusses a process for the synthesis of3,7-dioxo[4.1.0]heptane-2-imines by epoxidation under the oxidation of TBHP,and the compound is reacted under acidic conditions,the saccharide intermediate 3,7-dioxino[4.1.0]heptan-2-one can be obtained.