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One-pot Synthesis of Spirooxindole Derivatives in Water and Alkaline Proteinase-Catalyzed Henry Reaction

Author: DengXiang
Tutor: GuanZhi
School: Southwestern University
Course: Organic Chemistry
Keywords: Multicomponent reactions Green Catalysis Spiro oxindole derivatives Henry Reaction Alkaline protease
CLC: O643.32
Type: Master's thesis
Year: 2011
Downloads: 69
Quote: 0
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Abstract


In this paper, the main line of green catalysis, the spirit of \change the traditional synthetic route, the first report of the aqueous medium IRA-900 ion exchange resin catalysis \thereof. This thesis is divided into two parts: Part I: One-Pot Synthesis of Spiro aqueous hydroxy indole derivatives of spiro heterocyclic compounds are widely found in some natural products, with significant pharmacological activity and biological activity. Wherein the spiro oxindole derivatives are a very important class of spiro heterocyclic compounds, some natural product obtained has a better improve blood system to protect the brain and anti-tumor activity. Therefore spiro oxindole synthesis and properties of derivatives has been a research focus. We use water as solvent, isatin, malononitrile and 1,3 - dicarbonyl compounds (molar ratio of 1:1:1, are 1.0 mmol) the reaction between studied. First, the ion exchange resin as catalyst were investigated macroporous strong base anion exchange resin IRA-900 (CI-), A-26 (OH-) and macroporous strong acid cation exchange resin 50wx8-200 (H) catalytic effects, while the amount of the aqueous solvent, reaction temperature, etc. were screened a series of conditions. Ultimately selected to IRA-900 as the catalyst, 10 mL of water as the solvent and the reaction temperature is 25 ℃ optimum conditions, designed and synthesized a series of spiro oxindole derivatives, yield up to 99%. Secondly carried out without catalyst ideas and theoretical arguments, and through experiments found that the reaction can proceed smoothly, so our need for water solvent usage and reaction temperature range of conditions were screened to determine the case without catalyst, to 20 mL of water to do solvent and 80 ℃, temperature optimum reaction conditions were designed and synthesized a series of spiro oxindole derivatives, yield up to 93%. Part II: alkaline protease Henry Henry Reaction Catalyzed chemical synthesis reactions are an important class of carbon-carbon bond forming reactions, widely used in various types of natural products and in the synthesis of pharmaceutical intermediates. Meanwhile enzyme catalyzed reactions under mild conditions with high selectivity and fewer side effects, green, easy to purify the product, the catalyst can be recycled and other advantages. Given the advantages of enzyme-catalyzed reactions and Henry Reaction broad application prospects, and enzyme-catalyzed Henry Reaction little status quo. Enzyme used in this part as the catalyst for the 11 common enzymes were screened, of which the best catalytic effect of alkaline protease, alkaline protease we conditions in different solvents for the catalytic effect of experiments and found that the effect of the solvent in DMF the most ideal, identified as a catalyst and an alkaline protease in DMF as solvent optimal reaction conditions for different substrates Henry Reaction conducted in-depth research, and its yield up to 88%.

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