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Synthesis Of3-substituted Indole Derivatives And A Preliminary Study On The Proline-catalyzed Asymmetric Reactions

Posted on:2015-03-21Degree:MasterType:Thesis
Country:ChinaCandidate:C ChenFull Text:PDF
GTID:2251330428976135Subject:Biochemical Engineering
Abstract/Summary:PDF Full Text Request
Indole, which is of obvious pharmacological activity, is a fundamental parent structure of the natural products. Nowadays, the study on indole is still the focus of the chemistry research, specially for the C-3alkyl substituted indoles. Recently there are many construction method about C-3alkyl substituted indoles, however, more reports about the methods to constructe C-3alkyl substituted indoles from indoles are found this year.Hydrogen transfer reaction is kind of reaction which ultilize hydrogen donator as hydrogen resource to reacts with hydrogen receptor. Compared with the normal hydrogen reduction, this method has mild conditions, and don’t need high temperature and high pressure equipment. Hantzsch ester is a common hydrogen resource with the similar structure as coenzyme NADH, and it can effectively reduce the olefinic bood..Proline catalyst is a effective catalyst that can catalyze Adol, Micheal, Diels-Alder reaction etc with good selectivity. Improvement of the praline and the search for the praline catalyst of high selectivity are the recent research focus.In the basic conditions, the condensation of indole and aldehyde can result in3-hydroxy indole. In the acidic conditions, the hydroxyl group will leave by the catalysis, and then the α,β-unsaturated vinylogous imium forms. Subsequently, the imium is reduced by Hansch ester in order to get the3-substituted indole derivatives. After the systematic description of the effect made by acid, solvent, and substrate, we found the time of this kind reaction is short, but yield is high.In this paper, the author describe a method using praline to synthesize praline derivative as catalyst. Utilizing the catalysis, the Micheal addition between propaldehyde and α,β-unsaturated carbonyl compound, but the futher research is needed to get the ideal result.
Keywords/Search Tags:3-substituted indole, Hantzsch Ester, Hydrogen transfer reaction, L-proline, asymmetric synthesis
PDF Full Text Request
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