Synthesis of polysubstituted pyridines : Diels-Alder addition of 1-AZA-1, 3-dienes with acetylenic and ethylenic dienophil

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dc.contributor.advisor Behforouz, Mohammad en_US
dc.contributor.author Steizer, Lindsay S. en_US
dc.date.accessioned 2011-06-03T19:34:19Z
dc.date.available 2011-06-03T19:34:19Z
dc.date.created 1986 en_US
dc.date.issued 1986
dc.identifier LD2489.Z78 1986 .S74 en_US
dc.identifier.uri http://cardinalscholar.bsu.edu/handle/handle/183298
dc.description.abstract The synthesis of methyl 3,6-dimethylpyridine-2-carboxylate (192) by the Diels-Alder addition of 3-butene-2-one dimethylhydrazone (190) and methyl-2-butynoate (16) is described. The structure of 192 was confirmed by the synthesis of methyl 2,6-dimethylpyridine-3-carboxylate (195), the opposite regioisomer.The synthesis of methyl 3,5-dimethylpyridine-2-carboxylate (199) from [4+2] cycloaddition of 2-methyl-2-propenal dimethylhydrazone (171) and 16 is described. In addition to producing a small amount of 199 directly, the reaction produced an intermediate of possible structure 198 which yielded 199 on catalytic dehydrogenation.On prolonged heating, 2-acetyl-5-methylpyridine (200) was produced by the reaction of diene 171 with methyl vinyl ketone (176).The preparation of 2-cyan-5-methylpyridine (201) from the tetrahydropyridine derivative 175 via catalytic dehydrogenation is described.The synthesis of 5,7-dioxo-3-methyl-6-phenyl-1,1.,5,6,7-pentahydropyrroloC3,1.-b] pyridine (202) through the Diels-Alder addition of diene 171 and N-phenylmaleimide (149) is described. Also reported is the preparation of 5,7-dioxo-3-methyl-6-phenyl-3,5,6-trihydropyrrolo [3,1+-b]pyridine (203) via dehydrogenation of 202.
dc.description.sponsorship Department of Chemistry
dc.format.extent ix, 71 leaves : ill. ; 28 cm. en_US
dc.source Virtual Press en_US
dc.subject.lcsh Pyridine. en_US
dc.subject.lcsh Diels-Alder reaction. en_US
dc.title Synthesis of polysubstituted pyridines : Diels-Alder addition of 1-AZA-1, 3-dienes with acetylenic and ethylenic dienophil en_US
dc.description.degree Thesis (M.S.)
dc.identifier.cardcat-url http://liblink.bsu.edu/catkey/452401 en_US


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  • Master's Theses [5318]
    Master's theses submitted to the Graduate School by Ball State University master's degree candidates in partial fulfillment of degree requirements.

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