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AlCl3 Participated in Nucleophilic Substitution Reactions of Aryl Methaol Derivatives

Author: ZhangQingTao
Tutor: WuYangJie
School: Zhengzhou University
Course: Organic Chemistry
Keywords: Lewis acid Nucleophile Benzoxazole Isothiocyanate Isothiocyanate
CLC: O643.32
Type: Master's thesis
Year: 2011
Downloads: 8
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Abstract


This paper studies the Lewis acid AICl3 catalytic aryl carbinol compounds with ammonium thiocyanate reaction , to generate aryl isothiocyanates and aryl isothiocyanates (Scheme 1 ) . Isothiocyanate' dissertation">Isothiocyanate will be further reacted with an o - aminophenol reaction to generate a pharmaceutically active intermediate 2 - (di- aryl ) amino - substituted benzoxazole (Scheme2), drug intermediates for the therapeutic treatment of HIV Neural diseases, and inflammatory diseases . First with a Lewis acid the AICl3 catalyzed aryl methanol derivative with ammonium thiocyanate nucleophilic substitution reaction generates isothiocyanate (A) and the the isothiocyanate ester ( B ) . We found that the use of a stoichiometric amount of AICl3 as a catalyst, an air atmosphere , acetonitrile as solvent at -20 ° C C -containing electron - substituted benzyl alcohol can be obtained in high yield ( 67-99 %) of the isothiocyanate , the reaction effect of the electron withdrawing group - containing aromatic alcohols is poor ( 25-52 %) . Isothiocyanate B as raw materials o - aminophenol in THF were added to the base, an oxidizing agent , can be used to prepare 2 - (di- aryl) amino - substituted benzo ah oxazole ( 37-80 % ) [1] .

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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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