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Transition Metal-catalyzed Synthesis of Heterocyclic Compounds

Author: WuHaiSheng
Tutor: WangLei
School: Huaibei Normal
Course: Organic Chemistry
Keywords: Titanium Indium Iron 2,2 '- dihydroxybiphenyl Aromatic alkyne O-phenylenediamine Propargyl ester 1,3 - dipolar cycloaddition Azomethine ylides Lewis acid Regioselectivity Enantioselectivity
CLC: O643.36
Type: Master's thesis
Year: 2011
Downloads: 54
Quote: 0
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Abstract


Nitrogen, oxygen heterocyclic compound is a very important class of heterocyclic molecules, mostly having the biological and pharmacological activity. As pharmaceuticals, pesticides, natural medicines, dyes and other chemicals, intermediates, nitrogen, oxygen heterocyclic compounds and their derivatives used more and more widely in the production and life occupied an increasingly important position. Accordingly, synthetic nitrogen, oxygen heterocyclic compound is very necessary. So far, although there are a variety of methods can be used to build a nitrogen, oxygen heterocyclic compounds, find and develop innovative, efficient, environmentally friendly, mild reaction conditions, as well as operation and easy way to build a novel structure of the nitrogen-containing, oxygen-containing hetero the ring compounds skeleton still has a sustained demand. Constructed using metal-catalyzed organic reactions of nitrogen-or oxygen-containing compound is an effective strategy. Iron salt and indium salt having a cheap, low toxicity, etc., commonly used as a catalyst for organic reactions. Thesis cheap metal salt as a catalyst around the types of nitrogen-and oxygen-containing heterocyclic molecular design and synthesis method to carry out research work, including the following: (1) in this article to TiCl < sub> 4 as the catalyst, an aromatic alkyne by 2,2 '- dihydroxybiphenyl and end groups as a starting material, after the Michael addition reaction, and successful synthesis of a novel heterocyclic compound benzodioxepin heteroaryl derivatives Zhuo. The reaction only requires a catalytic amount (10 mol%) the TiCl 4 do not need to add any ligand under mild conditions, easy to operate, the product has a good regional selectivity and yield. (2) In this article, In (OTf) 3 catalyst, alkynyl esters and phthalic amines after [421] cycloaddition reaction synthesis disubstituted 1,5 - benzodiazepine derivatives. The method of the synthesis reaction at room temperature and solvent-free conditions, the reaction is mild, easy to operate, with the atom economy, and the catalyst is readily available and cheap raw materials, in line with the requirements of green chemistry. (3) The first study in this paper in order of FeCl 2 as catalyst, 3,5 - bis - (trifluoromethyl) diphenyl prolinol as chiral ligands used successfully in even the nitrogen azomethine ylides asymmetry [32] cycloaddition reaction. Under the conditions of 20 ° C, the choice CH 3 CN as solvent, NEt 3 as alkali, reaction under a nitrogen atmosphere for 24 h. The target product to get a good yield and enantioselectivity.

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CLC: > Mathematical sciences and chemical > Chemistry > Physical Chemistry ( theoretical chemistry ),chemical physics > Chemical kinetics,catalysis > Catalytic > Catalyst
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