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dc.contributor.authorCONNON, STEPHEN
dc.date.accessioned2011-03-01T16:47:55Z
dc.date.available2011-03-01T16:47:55Z
dc.date.issued2000
dc.date.submitted2000en
dc.identifier.citationS. J. Connon and A. F. Hegarty, Substituted 3,4-pyridynes: clean cycloadditions, Journal of the Chemical Society, Perkin Transactions 1, 1, 8, 2000, 1245, 1249en
dc.identifier.otherY
dc.identifier.urihttp://hdl.handle.net/2262/52932
dc.descriptionPUBLISHEDen
dc.description.abstractThe stabilisation of 3,4-pyridyne (1) by an alkoxy group adjacent to the ring nitrogen is reported. The regioselective lithiation of 2-ethoxy- (14), 2-methoxy- (18), 2-isopropoxy- (19) and 6-isopropoxy- (26) -3-chloropyridines with tert-butyllithium at low temperatures, followed by elimination of lithium chloride affords 2- and 6-alkoxy-3,4-pyridynes. These species are trapped in situ with furan in a Diels?Alder reaction to give 5?8 in 66?89% yield, and do not give products typical of polymerisation or nucleophilic addition to the 3,4-pyridyne intermediates. As a comparison treatment of 3-chloropyridine with furan and LDA gives only 19% of adduct (4). We also report the novel use of the isopropoxy (rather than methoxy) group in these systems, which can act as a heteroatomic electron donating group which inhibits ?-lithiation by tert-butyllithium because of its increased steric bulk.en
dc.format.extent1245en
dc.format.extent1249en
dc.language.isoenen
dc.publisherRoyal Society of Chemistryen
dc.relation.ispartofseriesJournal of the Chemical Society, Perkin Transactions 1;
dc.relation.ispartofseries1;
dc.relation.ispartofseries8;
dc.rightsYen
dc.subjectBiochemistryen
dc.titleSubstituted 3,4-pyridynes: clean cycloadditionsen
dc.typeJournal Articleen
dc.type.supercollectionscholarly_publicationsen
dc.type.supercollectionrefereed_publicationsen
dc.identifier.peoplefinderurlhttp://people.tcd.ie/connons
dc.identifier.rssinternalid23437
dc.identifier.rssurihttp://www.rsc.org/ej/P1/2000/a909772d.pdfen


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