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One-Pot Synthesis Of Polysubstituted Furans By The Catalysis Of FeCl3 And Synthesis Of 2-Phenylethanol And Isosolanone

Posted on:2010-06-30Degree:MasterType:Thesis
Country:ChinaCandidate:W H JiFull Text:PDF
GTID:2121360275989796Subject:Organic Chemistry
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The synthesis of furans has always been an area of intensive research by syntheticchemists due to their wide presence in a variety of natural products andchemists due to their wide presence in a variety of natural products andpharmaceuticals. In the past methods the preparation of furans needs advancedstarting material such as alkynones and allenones, and needs noble metal as catalyst, so it couldn't apply in large scale. For these reasons, the development of routes that allow the facile assembly of substituted furans under mild conditions from simple readily available starting materials remains an important objective.It has been knownγ-alkynyl ketones may be cyclized to furans under acidicconditions. It seems that this route to furans has been limited by ready access toγ-alkynyl ketones and by moderate yields in the cyclization step. We has been developed an efficient FeCl3-catalyzed propargyltion/cycloisomerization tandem reaction of propargylic alcohols or acetates with 1,3-dicarbonyl compounds, leadingto the synthesis of substituted furans (Figure 1).Functional groups,such as chloro,bromo, ester and methoxyl were tolerant in the tandem process, which allow an access to other functionalized furans.β-Phenylethanol (also known as 2- phenylethanol and PEA) is aromatic alcohols with the aroma of roses. It is widely applied in various industrial fields,such as medicament, food, cosmetic, tobacco, and chemical. At presentβ-phenylethanol synthesis with the benzene-oxirane craft account for 40% of market share.Recently, We developed a simple method to synthesizeβ-Phenylethanol from L-phenylalanine in 45% overall yield (Figure 2), modeled on the biological degradation of the " phenyl-pyruvic acid " method.Isosolanone is one of the key tobacco fragrance compounds. It plays an important role in the quality of tobacco. We synthesize isosolanone from 3-methyl butanal in five steps with an overall yield of 22% (Figure 3).
Keywords/Search Tags:iron(III) chloride, furans, propargylic alcohols, phenylethanol, isosolanone
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