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The Application of Isocyanides in the 1, 3-Dipolar Cycloaddition Reactions

Author: QianBo
Tutor: LiangYongMin
School: Lanzhou University
Course: Applied Chemistry
Keywords: Multi-component reaction Isocyanurate Butyne Dimethyl 1,3 - dipolar cycloaddition reaction 1,3 - dipole Azomethine imine Pyrazole derivative
CLC: O621.25
Type: Master's thesis
Year: 2009
Downloads: 100
Quote: 0
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Abstract


Multi-component reactions (MCRs) speed , high efficiency , environmentally friendly characteristics extensive attention has been more than a century , the typical reaction is a class of multi-component reactions ( IMCRs ) isocyanurate participation its more diversified Beishouqinglai . In recent years , the nucleophile with the electrophilic π- electron system zwitterionic intermediates formed by the addition reaction of the rapid development of applications in organic synthesis reaction , which is the most representative isocyanurate and the butyne acid dimethyl the intermediates formed in the ester (DMAD) Michael addition . Under normal circumstances, they are still maintained in the further reaction , the nature of the nucleophilic and in the majority of the reaction , not only as a catalyst to catalyze the reaction , but also as a reaction of the substrate is fully or partially retained in the resulting product . 1,3 - dipolar cycloaddition reaction is a classic cycloaddition reaction azomethine imine ylides as 1,3 - dipole participate in cycloaddition reactions , build two bridgehead nitrogen atoms heterocyclic system , attracting more and more attention of chemists . Isocyanurate by 1,3 - dipolar cycloaddition reaction build Heterocyclic Compounds were chloroform as a solvent and heated to reflux for 12 hours under the conditions of the isocyanurate butyne Dimethyl and 1,3 - dipole occurred to the \The structure of the product by X-ray single crystal diffraction , NMR, IR , elemental analysis , and testing means determined . Through systematic analysis of the electronic and three-dimensional structure of a series of products , in the previous work done by the foundation , the mechanism of this reaction to speculate the following conclusions: as nucleophiles isocyanurate and activation π-electron system butynyl dimethyl Michael addition reaction occurs after the formation of a zwitterionic intermediate , and then by another molecule electrophilic reagent - 1,3 - out of the dipole with a five- membered ring the azomethine imines capture thereby cyclized to pyrazole derivatives .

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CLC: > Mathematical sciences and chemical > Chemistry > Organic Chemistry > Organic Chemistry general issues > Properties of organic compounds > Chemical properties of organic reactions
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