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Synthesis Of Thieno [2,3-b] Thiopyran Via Domino Process

Posted on:2006-07-09Degree:MasterType:Thesis
Country:ChinaCandidate:J Q ZhangFull Text:PDF
GTID:2121360152986593Subject:Organic Chemistry
Abstract/Summary:PDF Full Text Request
α-Oxo ketene dithioacetals 1 are a kind of versatile intermediates in organic synthesis. It can be widely used as 1,3-electrophile or nucleophilic reagent to form aromatic and heterocyclic compounds.Green synthesis is emerging as a new frontier in organic synthesis. Therefore it is very important to explore the feadibility of clean synthesis lf complex compounds from α-oxo ketene dithioacetals In this thesis , 3-(4-(bromomethyl)-1, 3-dithiolan-2-ylidene )pentane-2, 4-dione was synthesized from pentane-2, 4-dione firstly, their reactions Such as (1) dehydrobromogenation,(2) condensation with arylaldchydes were investigated, 3-(4-methyl-1, 3-dithiol-2-ylidene) pentane-2, 4-dione and 4-(4-methyl-1, 3-dithiol-2-ylidene)-1, 7-diaryl-1, 6-diene-3, 5-dione, a kind of complicated polycycles, were obtained, using 4-(4-methyl-1,3-dithiol-2-ylidene)-1, 7-diaryl-1, 6-diene-3, 5-dione with α.ωd?iamines are performed. An new and effective atom economy, domino reaction is developed, and 5, 6dihydro-4H-thieno [2, 3-b] thiopyran are synthesized by 4-(4-methyl-1, 3-dithiol-2-ylidene)-1, 7-diaryl-1, 6-diene-3, 5-dione The factors influencing the reactions mentioned and the relative mechanisms were discussed. The vista for the further work was based on correlative documents. 21 new compounds were prepared Inthesis and were confirmed by IR and 1~H NMR.13C NME...
Keywords/Search Tags:α-oxo ketene dithioacetals, thieno[2, 3-b]thiopyran, green syntnesis, atom economy, dominoes reaction
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