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  • 1
    Electronic Resource
    Electronic Resource
    Diastereoselective Synthesis of 1-Hydroxy-Substituted Benzo[b]quinolidines and 11-Hydroxy-Substituted Azepino[1,2-b]isoquinolines via Hetero-Ene Cyclization (1997)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1997 (1997), S. 533-540 
    Details
    ISSN: 0947-3440
    Keywords: Ene reaction ; Benzo[b]quinolidines ; Azepino[1,2-b]isoquinolines ; Lewis acid catalysis ; Nitrogen heterocycles ; Cyclizations ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: (L)-Phenylalanine 4 can be converted to N-(4-methyl-3-pentenyl)tetrahydrosisoquinoline-3-carbaldehyde 10 and the corresponding homologous aldehyde 19 in 4 and 5 steps, respectively, by employing the Pictet-Spengler reaction as the key step. After Lewis acid catalyzed cyclization of 10 and 19 the cis-configured 1-hydroxybenzo[b]quinolizidine 21a and 11-hydroxyazepino[1,2-b]isoquinoline 22a were obtained with high diastereoselectivities. Compound 21a, which was characterized by X-ray structure analysis, displays a fishbone pattern of endless zig-zag chains connected via intermolecular hydrogen bonds in the solid state.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199719970314
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  • 2
    Electronic Resource
    Electronic Resource
    New Synthetic Pathways to Nitrogen Heterocycles (1997)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1997 (1997), S. 1-11 
    Details
    ISSN: 0947-3440
    Keywords: Nitrogen heterocycles ; Imines ; Hetero-Diels-Alder reaction ; Hetero-ene reaction ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Novel Lewis acid-catalyzed cyclizations of N-arylimines and N-benzylimines derived from amino acids and terpenes allow the diastereoselective preparation of octahydroacridines, indolizino[3,4-b]quinolines, indolizidines, quinolizidines and piperidines. Although these two types of reactions can be classified as formal hetero-Diels-Alder and hetero-ene reactions respectively, both proceed stepwise via cationic intermediates, which allow stereochemical control via chelate complexes. Stereochemical and mechanistical studies are described briefly.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199719970104
    Library Location Call Number Volume/Issue/Year Availability
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    Paper (German National Licenses)
    Fulltext
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