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Study On The Synthesis Of Pyrrolidone,Acetylamide,Furanone Compounds Starting From Isonitrile Compounds

Posted on:2018-06-25Degree:MasterType:Thesis
Country:ChinaCandidate:Y HeFull Text:PDF
GTID:2481305420985999Subject:Organic Chemistry
Abstract/Summary:PDF Full Text Request
Over the last few decades,the use of isocyanides in organic synthesis1 has played a pivotal role in the generation of chemical diversity,which has been exploited both in organic and medicinal chemistry,and in polymer science.Isocyanides are important C1 building blocks in organic synthesis and these molecules are known to take part in several of different types of reaction,especially finding particular usefulness in a wide variety of isocyanide-based multicomponent reactions.In scientific point of view,the functionalization of unsaturated hydrocarbon is of great importance due to promoting the advancement of human material civilization and its core position in scientific development.The research around the substances conversion reactions of unsaturated hydrocarbon is the source and power of chemistry development.Consequently,we presumed that isocyanide insertion should offer tremendous opportunities for the synthesis of fine nitrogen-containing compounds and participate in catalytic reactions from unsaturated hydrocarbon.(1)Isocyanides have been widely applied to construct various nitrogen heterocyclic compounds due to their superior capability to rapidly create molecular diversity,however,most reported achievements mainly focus on the utility of isocyanides single insertion for the synthesis of nitrogen-containing compounds.Only a few examples of metal-catalyzed double isocyanides insertion have been reported.We have successfully presented a synthetic route for the synthesis of 5-iminopyrrolones via isocyanide double insertion and cycloaddition reaction with the one-pot combination of Pd(dppf)Cl2/Cu(OAc)2.Good yields,high regioselectivity,easily available starting materials and simple operation make it an attractive alternative to the contemporary synthetic routes.(2)Alk-2-ynamide(?,?-alkynylamide)derivatives are important building blocks in organic synthesis and often fundamental scaffolds of pharmaceutically relevant compounds.This class of compounds plays a crucial role in natural products as well as key intermediates in the synthesis of heterocycles.Isocyanides are important C1 building blocks in organic synthesis and these molecules are known to take part in several of different types of reaction,especially finding particular usefulness in a wide variety of isocyanide-based multicomponent reactions.This reaction provides mild conditions to afford a variety of useful alk-2-ynamide by Pd catalysis in an efficient way.(3)The synthesis of furanones has attracted tremendous interest in the past decades because of the importance of these five-membered heterocycles in biologically active natural products1 and pharmacologically interesting compounds.An efficient and straightforward one-pot strategy for the synthesis of furan-3(2H)-one derivatives from propargylic ketones in the presence of Cu(OAc)2/tBuNC is described.
Keywords/Search Tags:Isocyanides, Unsaturated hydrocarbon, 5-Iminopyrrolones, ?,?-Alkynylamide, Furanones
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