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  • Synthesis and transformations of some N-substituted (1R,4S)-3-aminomethylidene-1,7,7-trimethylbicyclo[2.2.1]-heptan-2-ones
    Grošelj, Uroš ...
    Acid-catalysed reactions of (1R,3E,4S)-3-[(dimethylamino)methylidene]-1,7,7-trimethylbicyclo[2.2.1]hept an-2 -one (2) with amino acid derivatives 3a-d and pyrazolidin-3-ones 5a-e gave the ... substitution products 4/4a-d and 6a-e, respectively, in 40-83% yields. Compound 4a was transformed with Bredereckćs reagent into the 3-(dimethylamino)propenoate 7/7. Treatment of 1-{[(1R,3Z,4S)-1,7,7-trimethyl-2-oxobicyclo-[2.2.1]hept-3-ylide-ne]methyl}p yrazolidin-3-ones 6a and 6b with dimethyl acetylenedicarboxylate in refluxing anisole furnished the corresponding cycloadducts as mixtures of four diastereomers, the major endo-isomers 10/11a,b and the minor exo-isomers 12/13a,b with moderate endo-selectivity. Chromatographic separation of 10/11/12/13a,b afforded the endo/exo-pairs of diastereomers, 10/13a,b and 11/12a,b. The structures of compounds 4/4, 6, 7/7, and 10/11/12/13were determined by NMR and by X-ray diffraction.
    Vir: Acta chimica slovenica. - ISSN 1318-0207 (Vol. 53, no. 3, 2006, str. 245-256)
    Vrsta gradiva - članek, sestavni del
    Leto - 2006
    Jezik - angleški
    COBISS.SI-ID - 27954437

    Povezava(-e):

    Digitalna knjižnica Slovenije - dLib.si

vir: Acta chimica slovenica. - ISSN 1318-0207 (Vol. 53, no. 3, 2006, str. 245-256)

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