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Tandem Synthesis of Pyranocoumarin Derivatives

Author: HeZhenXing
Tutor: WangYanGuang；LinXuFeng
School: Zhejiang University
Course: Chemistry
Keywords: 4 - hydroxycoumarin 1,3 - diaryl- propene α, β- unsaturated ketone DDQ Lewis acid C-H bond activation
CLC: TQ252
Type: Master's thesis
Year: 2010
Downloads: 163
Quote: 0
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Abstract


New methods of organic synthesis of heterocyclic compounds having biological activity has been the frontier and hot organic chemistry . The thesis of two reactors in series , can be obtained from simple starting materials pyrano coumarins . Main contents are as follows : 1. Studied a DDQ participation through two CH bond activation reaction synthesis pyrano coumarin compounds. The starting material of the reaction of 4 - hydroxy- coumarin and derivatives thereof and 1,3 - diaryl acrylic compound. In DDQ oxidation , through two successive series CH bond activation, thereby synthesized a series of pyran derivatives of coumarin . We design the intermediate substrate that the final product is to ring at DDQ oxidation occurs under , further evidence of the proposed mechanism . Reaction process of allylic cation radicals , the asymmetric 1,3 - diaryl acrylic compound , the reaction has two isomers. The reaction is readily available raw materials preparation , easy to operate , no heavy metal ions involved . (2) development of a Lewis acid catalyzed 4 - hydroxycoumarin derivatives and chalcone tandem reaction . This reaction provides an alternative synthesis of coumarin derivatives, pyran new method . Through the process of the reaction is: BF 3 · Et 2 O catalyzed 4 - hydroxycoumarin on α, β- unsaturated ketone 1,4 - addition to give addition product , and then in BF 3 · Et 2 O -catalyzed intramolecular nucleophilic attack occurs once , and then get off part of the water the final cyclization product. The reaction material is simple , mild reaction conditions .

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CLC: > Industrial Technology > Chemical Industry > Basic Organic Chemistry Industry > The production of heterocyclic compounds > Containing five pairs or more different atoms of heterocyclic
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