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Ring Closing Enyne Metathesis Of Imidazole Derivatives And Subsequent Diels-Alder Reaction

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Ring Closing Enyne Metathesis Of Imidazole Derivatives And Subsequent Diels-Alder Reaction

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dc.contributor.author Ekanayake, E. Vindana en_US
dc.date.accessioned 2008-08-08T02:31:03Z
dc.date.available 2008-08-08T02:31:03Z
dc.date.issued 2008-08-08T02:31:03Z
dc.date.submitted December 2007 en_US
dc.identifier.other DISS-1925 en_US
dc.identifier.uri http://hdl.handle.net/10106/901
dc.description.abstract The work presented in this thesis describes the development of new synthetic routes to elaborate simple imidazole derivatives into complex imidazole molecules by the application of different sequential transformations. The first transformation considered is the ring closing enyne metathesis (RCEYM) of imidazoles. To carry out this reaction various allyl and propargyl derivatives of imidazole have been synthesized. These enyne substrates have been varied by changing the positions on the imidazole, as well as changing the protecting groups. All substrates contain trimethysilyl-protected propargyl derivative as the "yne" moiety. After the successful preparation of different enyne substrates, they were subjected to the metathesis reaction using Grubbs' second generation catalyst. The majority of enyne substrates participated RCEYM smoothly to produce the expected diene derivatives in moderate yields. The next transformation employed was the Diels-Alder (DA) reaction on the diene derivatives obtained from the RCEYM reaction. For this transformation, first N-phenylmaleimide has been used as the dienophile with the diene substrates and all these cycloaddition reactions provided the expected cycloadduct in good yields. Finally, different dienophiles have been used for the DA reaction using one of the diene produced by RCEYM of dimethylaminosulfamoyl (DMAS) protected enyne substrate. These DA reactions also resulted in the expected cycloadducts in good yields. Unexpected results have been observed from two of the substrates while attempting the metathesis reaction. en_US
dc.description.sponsorship Lovely, Carl en_US
dc.language.iso EN en_US
dc.publisher Chemistry & Biochemistry en_US
dc.title Ring Closing Enyne Metathesis Of Imidazole Derivatives And Subsequent Diels-Alder Reaction en_US
dc.type M.S. en_US
dc.contributor.committeeChair Lovely, Carl en_US
dc.degree.department Chemistry & Biochemistry en_US
dc.degree.discipline Chemistry & Biochemistry en_US
dc.degree.grantor University of Texas at Arlington en_US
dc.degree.level masters en_US
dc.degree.name M.S. en_US
dc.identifier.externalLink https://www.uta.edu/ra/real/editprofile.php?onlyview=1&pid=30
dc.identifier.externalLinkDescription Link to Research Profiles

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