Studies On A New Method Of Synthesizing 3-thiolated Indole Compounds And(Z)-?-Sulfonyl Enoates Compounds

3-thiolated indole compounds are very important indole derivatives containing sulfur atoms,which are widely applied in medicine,materials and agriculture.In recent years,there are many methods for the synthesis of 3-thiolated indole compounds.The most widespread method is the direct thiolation of indole and sulfur-containing reagents,and the C-S bond is formed at the 3 position of indole.The most widely used sulfur-containing reagents including thiol/thiophenol,disulfide compound and sulfonic acid derivatives,this method is favored by many organic chemists due to its good substrate compatibility,wide source of sulfur source and no need for prefunctional transformation of indole.(Z)-?-Sulfonyl Enoates are a class of enoates containing sulfonyl groups.Their structural units exist widely in many natural products and many drugs.They are widely applied in the field of organic synthesis as the blocks of building biological macromolecules.At present,there are many methods to synthesize this kind of compound,but all of them have some inadequacies,such as tedious operation,harsh conditions and unstable raw materials.The content of this thesis is two parts.The part one is the synthesis of 3-thiolated indole compounds with sulfonyl chloride and indole compounds as raw materials through a series of reduction,addition,and elimination reaction processes Under the action of tetrabutylammonium iodide.The part two is successfully synthesized(Z)-?-Sulfonyl Enoates compound Under the action of acid.The results of the main research work are as follows:1.A method for constructing C-S bond by functionalization of indole compound 3 site C-H bond is realized,The efficient synthesis of 3-thiolated indole compound was successfully realized.This system features mild conditions,simple operation,highly regioselective and shows a wide substrate application leading to excellent yields.2.A mild,rapid and efficient method for stereoselective synthesis of(Z)-p-Sulfonyl Enoates compounds is explored.In this experiment,sodium sulfonate compounds and propargyl esters compounds are used as raw materials.Under the action of acid,the target products can be prepared by a simple addition reaction.The method is fast,environmental friendly,and has wide application scope and good stereoselectivity.