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The Synthesis of Aziridines and Its Ring-opening Reaction by Glucose

Author: LiZhongBo
Tutor: ZhangMingJie
School: Tianjin University
Course: Organic Chemistry
Keywords: Aziridination Ring-opening reaction Aminoglycosides Ligand
CLC: TQ251
Type: Master's thesis
Year: 2010
Downloads: 88
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Abstract


Aziridination derivative is an important member of the block in organic synthesis and the intermediate the saccharide compound nucleophilic ring opening product obtained : aminoglycoside compounds are a class of very special biological activity and biological function compounds in clinical . In this thesis, nitrenes olefin addition reaction of carbene imine addition reaction of two different methods to achieve the the Aziridination reaction synthesis of the two types of 16 - Aziridination , of which there are two are novel compounds . In the nitrenes olefins reaction , selected from low-cost and easy to get green chloramine -T is nitrogen transfer reagent , examined in detail the analysis of the main factors of the the impact Aziridination reaction , optimization of the reaction conditions on the basis of , NBS catalyst synthesized the seven ring is connected to the supply base Aziridination , and the catalyst suction the olefin synthesis Aziridination power base is connected to the double bond made ??an attempt to optimize the reaction conditions found the NBS role in promoting the olefin synthesis Aziridination electron withdrawing group is connected with a double bond . We selected the Py HBr3 as catalyst a ring with electron-withdrawing Aziridination for substrate synthesis Aziridination the feasibility and coumarin was analyzed and discussed . Carbene addition reaction of the imine , we synthesized a 15 - imine compound in chloroform as the reaction solvent to generate carbene with an imine addition reaction under alkaline conditions , synthesis of the eight corresponding nitrogen heterocyclic propane, and the reaction of the imine substrates made ??analyzed . The important position of the of aminoglycoside compounds in the field of medicine , we use benzoyl protected glucoside nucleophile on the four Aziridination ring-opening reaction , not been reported on four literature the glucosaminidase compounds are a good yield . In addition, we also synthesized a new ligand and two lactone spices , laid the foundation for the exploration on the the Aziridines asymmetric synthesis .

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CLC: > Industrial Technology > Chemical Industry > Basic Organic Chemistry Industry > The production of heterocyclic compounds > Five heterocycles containing a single different atoms
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