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Synthesis Of 3-substituted Indole Derivatives Catalyzed By Br?nsted Acidic Ionic Liquid

Posted on:2011-09-07Degree:MasterType:Thesis
Country:ChinaCandidate:C J YuFull Text:PDF
GTID:2121360305987337Subject:Organic Chemistry
Abstract/Summary:PDF Full Text Request
1,2,3-triazole and pyrazole structural units are so biologically active that experts from the areas of orgaic synthesis and medical synthesis pay more attetion to them. Indole as an important kind of heterocyclic compounds is applied widely in medical chemistry, agricultural chemistry, material science and so on. Recently, 3-substituted indoles especiallyβ-indolylketones and bis-indolylmethanes have been one of the most active areas in indole chemistry.Ionic liquids entirely composed of cations and anions were liquid in room temperature. They have recently been attracted much attention in organic synthesis, catalysis and electrochemistry due to their unique properties such as nonvolatile, high thermal stability and good conducting ability. In view of this, this article used acidic ionic liquids as catalysts to synthesize a series of 3-substituted indole derivatives containing pyrazolyl or 1,2,3-triazolyl and reaction conditions were optimized.This thesis consists of two major parts:The first part is about literature review. The progress introduced the ionic liquid, bis-indolylmethane andβ-indolylketones.The second part is about experimental content. Major work as follows:1. The systhesis ofβ-indolylketones by the reaction of indole and chalcone using br?nsted acidic ionic liquid as catalyst.2. The systhesis ofβ-indolylketones containing 1,2,3-triazolyl by the reaction of indole andα,β-unsaturated carbonyl compounds using br?nsted acidic ionic liquid [Sbmim][HSO4] as catalyst.3. The Michael addition reaction of indoles to 4-arylmethyl-3- methyl-1-phenylpyrazol-5-one catalyzed br?nsted acidic ionic liquid [BSbbt][HSO4].4. The systhesis of bis-indolylmethanes containing 1,2,3-triazolyl or pyrazolyl by the reaction of indole and 4-formyl-1,2,3-triazol or 4-formylpyrazole using br?nsted acidic ionic liquid [PyNCH2CO2H][HSO4] as catalyst.The structures of new compounds were confirmed on the basis of 1H NMR, MS, IR spectrum and element analysis.
Keywords/Search Tags:Br(?)nsted acidic ionic liquid, bis-indolylmethane, β-indolylketone, 1,2,3-triazole, pyrazole
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