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Study on Synthesis of Benzopyrone

Author: CaiShuYing
Tutor: WangYanGuang；LvPing
School: Zhejiang University
Course: Organic Chemistry
Keywords: benzo-α-pyrone benzo-γ-pyrone 3-(2-hydroxyphenyl) propiolate iodine DMF trifluoroborane etherate
CLC: O621.25
Type: Master's thesis
Year: 2012
Downloads: 145
Quote: 1
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Abstract


Benzopyrones are an important class of organic heterocyclic compounds which have attracted much attention because of their attractive bioactivities. In this dissertation, we respectively synthesized benzo-a-pyrones and benzo-y-pyrones from 3-(2-hydroxyphenyl)propiolates and the results are listed as below:1. We developed a reaction between 3-(2-hydroxyphenyl)propiolate and iodine in toluene, which afforded 3,4-diiodobenzo-a-pyrone in high yield. Moreover, the skeleton of benzo-y-pyrone was constructed from 3-(2-hydroxyphenyl)propiolate and DMF in the presence of iodine.2. We developed a novel synthetic method leading to the formation of 2,3-substituted-2H-chromen-4-ol from 3-(2-hydroxyphenyl)propiolate and aldehyde in the presence of trifluoroborane etherate. One of products was further oxidized by DDQ and a benzo-y-pyran ketone was constructed.

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CLC: > Mathematical sciences and chemical > Chemistry > Organic Chemistry > Organic Chemistry general issues > Properties of organic compounds > Chemical properties of organic reactions
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