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Study On The Organic Reactions In Aqueous Media

Posted on:2009-02-23Degree:MasterType:Thesis
Country:ChinaCandidate:Z J BaoFull Text:PDF
GTID:2121360245960531Subject:Organic Chemistry
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This paper contains four aspects. We describe the study on synthesis of allylation, tetrahydrobenzo[b]pyran mainly in water in the first three aspects. Last, we describe the study on asymmetric addition of terminal acetylenes to aldehydes.Firstly, we described allylation of aryl trichloromethyl ketones in aqueous media. We reported the indium-mediated allylation to a wide variety of trichloromethyl ketones. The simple work of procedure, mild reaction conditions make our methodology a valid contribution to the existing processes in the field of allylation.Secondly, we studied one pot synthesis of 2-amino-7,7-dimethyl-5-oxo-4-aryl- 4H-chromene-3-carbonitrile-5,6,7,8-tetrahydrobenzo[b]pyran in water with aldehyde, 5,5-dimethyl-1,3-cyclohexadion, malononitrile. We could also get good yields without catalyst,and make solvent more green.Thirdly, we studied synthesis of 2-amino-7,7-dimethyl-5-oxo-4-aryl-4H- chromene- 3-carbonitrile-5,6,7,8-tetrahydrobenzo[b]pyran in NCW (near-critical water). Better results are also obtained under the condition of catalyst free.Finally, we did a pilot study on addition of terminal acetylenes to aldehydes. Addition of terminal acetylenes to aldehydes in the presence of resin-supported chiral catalyst were detected with good ee values, the recycle of catalyst were discussed as well.
Keywords/Search Tags:aqueous media, allylation, benzo[b]pyran, asymmetric reaction
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