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  • 1
    Electronic Resource
    Electronic Resource
    Zur Autoxidation von cyclischen Iminen, II. Synthese von Chinolizidin-Derivaten (1982)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 115 (1982), S. 1626-1635 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Autoxidation of Cyclic Imines, II. Synthesis of Quinolizidine DerivativesAutoxidation of bicyclic imines 4a-d and 18a, b yields Δ9-dehydro-4-quinolizidone derivatives 6 and 20, respectively. Mostly, the quinolizidine compounds are formed via labile α-iminohydroperoxides by fragmentation and rearrangement. For some cases the described reaction is a preparative useful route to quinolizidine derivatives, since the starting imines are easily available.
    Notes: Die Autoxidation von bicyclischen Iminen 4a-d und 18a, b führt über eine Fragmentierung der als instabile Zwischenprodukte entstehenden α-Iminohydroperoxide zu Δ9-Dehydro-4-chinolizidon-Derivaten 6 bzw. 20. Die Bildung weiterer Produkte der Autoxidation wird diskutiert. In einigen Fällen stellt diese Umlagerung eine präparativ geeignete Darstellung von Chinolizidin-Derivaten dar, da die Synthese der Ausgangs-Imine einfach ist.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19821150437
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  • 2
    Electronic Resource
    Electronic Resource
    Zur Autoxidation von cyclischen Iminen, I (1979)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 112 (1979), S. 734-742 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Autoxidation of Cyclic Imines, IIn a noncatalyzed reaction cyclic imines, e. g. 1a-d, bearing one or two α-tert. carbon atoms are oxidized by molecular oxygen. Usually, the products are relatively unstable α-iminohydroperoxides, which are subject to further rearrangement or reduction. These compounds are partially further oxidized. The isolation of the products as well as their structure elucidation by spectroscopic methods are established.
    Notes: Cyclische Imine mit einem oder zwei tert. α-C-Atomen, z.B. 1a-d, werden durch nichtsensibilisierten Sauerstoff oxidiert. Primär entstehen dabei meist instabile α-Iminohydroperoxide, die Folgereaktionen wie Umlagerung und Reduktion eingehen. Diese Verbindungen werden teilweise erneut oxidiert. Die Produkte der Autoxidation werden isoliert und ihre Konstitutionen ermittelt.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19791120235
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  • 3
    Electronic Resource
    Electronic Resource
    Eine weitere Synthese von (±)-Lycopodin (1982)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1982 (1982), S. 1700-1705 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: A Further Synthesis of (±)-LycopodinThe synthesis of (±)-lycopodin from 2-cyanoethyl-5-methyl-1,3-cyclohexanedione (2b) in six steps is described. An important step is the stereoselective 1,3-annulation reaction of the unsaturated imine 4b with acetone dicarboxylic acid yielding the tricyclic ketone 5b.
    Notes: Die Synthese von (±)-Lycopodin (1) aus 2-Cyanethyl-5-methyl-1,3-cylohexandion (2b) in sechs Stufen wird beschrieben. Ein wichtiger Syntheseschritt ist die stereoselektive 1,3-Anellierung des ungesättigten Imins 4b mit Acetondicarbonsäure zum tricyclischen Keton 5b.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198219820910
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  • 4
    Electronic Resource
    Electronic Resource
    Synthese des Lycopodium-Alkaloids (±)-Acetylflabellidin über 1,3-Anellierung von Eniminen (1982)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1982 (1982), S. 2057-2061 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Synthesis of the Lycopodium Alkaloid (±)-Acetylflabellidine via 1,3-Annulation Reactions of EniminesThe 1,3-annulation reaction of 2,3,4,5-tetrahydro-6-methylpyridine (11) with the enimine 7 catalyzed by perchloric acid and subsequent acetylation stereoselectively yield the tetracyclic adduct 2 as the main product, the structure and relative configuration of which are in agreement with the acetyl derivative of the Lycopodium alkaloid flabellidine (1).
    Notes: Die durch Perchlorsäure katalysierte 1,3-Anellierung von 2,3,4,5-Tetrahydro-6-methylpyridin (11) an das Enimin 7 mit anschließender Acetylierung liefert in stereoselektiver Reaktion als Hauptprodukt das tetracyclische Addukt 2, dessen Struktur und relative Konfiguration mit dem Acetylderivat des Lycopodium-Alkaloids Flabellidin (1) identisch ist.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198219821111
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  • 5
    Electronic Resource
    Electronic Resource
    Synthese des Lycopodium-Alkaloids rac-α-Obscurin durch 1,3-Anellierung eines Enimins (1983)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1983 (1983), S. 220-225 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Synthesis of the Lycopodium-Alkaloids rac-α-Obscurin through 1,3-Anullation of an EnimineAcid catalysed 1,3-annulation of 1,2,3,4-tetrahydro-6-methyl-2-oxopyridine (1) to the enimine 3, followed by methylation, provides a new regio and stereoselective route to rac-α-obscurine (5). Reduction of rac-N-demethyl-α-obscurine with LiAlH4 yields rac-lycodine (11) and rac-deacetyl-flabellidine (9). A new pathway for the biogenesis of the β-amino-imine 9 is suggested.
    Notes: Die säurekatalysierte 1,3-Anellierung von 1,2,3,4-Tetrahydro-6-methyl-2-oxopyridin (1) an das Enimin 3 liefert nach anschließender Methylierung regio- und stereoselektiv rac-α-Obscurin (5). Reduktion von rac-N-Desmethyl-α-obscurin (4) mit Lithiumaluminiumhydrid führt zur Bildung von rac-Lycodin (11) und rac-Desacetylflabellidin (9). Für das β-Amino-Imin 9 wird ein neuer Biogeneseweg vorgeschlagen.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198319830206
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  • 6
    Electronic Resource
    Electronic Resource
    Synthese des Lycopodium-Alkaloids rac-Lucidulin aus Hexahydro-7-methylchinolin (1984)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1984 (1984), S. 1519-1528 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Synthesis of the Lycopodium Alkaloid rac-Luciduline from Hexahydro-7-methylquinolineThe 1,4 addition of malonic acid to the eneimine functional group of 2 leads to diastereomeric imines which via disproportionation can be transformed into the pyridine derivative 9. From 9 the ester 5b is obtained stereoselectively. Oxidation of 5b with potassium permanganate and crown ether yields the lactam ester 15. The cyclization and transformation of 15 into rac-luciduline (1) is described. 5b can also be obtained in a simple, nonstereoselective synthesis from the ketone 10.
    Notes: Durch 1,4-Addition von Malonsäure an die Eniminfunktion in 2 entstehen diastereomere Imine, die sich durch Disproportionierung in das Pyridinderivat 9 umwandeln lassen. Stereoselektiv wird daraus der Ester 5b gewonnen, der mit Kaliumpermanganat und Kronenether den Lactamester 15 liefert. Die Cyclisierung und Umwandlung von 15 zum rac-Lucidulin (1) ist beschrieben. Der Ester 5b wird in einer einfachen, nicht stereoselektiven Synthese auch aus dem Keton 10 erhalten.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198419840812
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  • 7
    Electronic Resource
    Electronic Resource
    Bildung von Oxetanen bei der photosensibilisierten Oxidation von Enaminen (1985)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 118 (1985), S. 1927-1935 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Formation of Oxetanes via Photo-sensitized Oxidation of EnaminesPhotooxidations of the enamines 1 and 5 in toluene give rise to the formation of the usual reaction products. In methanol, however, the oxetanes 8 and 13, respectively, are isolated as the main photooxidation products. Both the mechanism of their formation as well as some reactions of 8 and 13 are discussed. Oxidation of 13 with m-chloroperbenzoic acid produces the aldehyde 15 via a multi-step reaction.
    Notes: Die Photooxidation der Enamine 1 bzw. 5 in Toluol liefert die erwarteten Reaktionsprodukte. In Methanol entstehen dagegen die Oxetane 8 bzw. 13 als Hauptprodukt der Photooxidation. Die Reaktionen dieser Verbindungen werden beschrieben. Die Oxidation von 13 mit m-Chlorperbenzoesäure führt über einen mehrstufigen einheitlichen Reaktionsablauf zum Aldehyd 15. Der Bildungsmechanismus der Oxetane 8 und 13 wird diskutiert.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19851180517
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