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  • 1
    Electronic Resource
    Electronic Resource
    Intramolekulare Aromatenalkylierungen, III1) Synthese von N-Methyl-8-phenyl-1,2,3,5,6,7,8,8a-octahydrochinolin (1975)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1975 (1975), S. 1081-1091 
    Details
    ISSN: 0075-4617
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Intramolecular Alkylations of Aromatic Compounds, III1).  -  Synthesis of N-Methyl-8-phenyl-1,2,3,5,6,7,8,8a-octahydroquinolineThis contribution reports the synthesis of N-methyl-8-phenyl-1,2,3,5,6,7,8,8a-octahydroquinoline (3) from 8-phenyl-5,6,7,8-tetrahydroquinoline (7), which in turn has been obtained for the first time from a mixture of the isomeric enamines 8a and 8b. Surprisingly, attempts to prepare 7 from 8-aza-1-tetralone (13) and organometallic reagents failed.
    Notes: Es wird die Synthese von N-Methyl-8-phenyl-1,2,3,5,6,7,8,8a-octahydrochinolin (3) aus 8-Phenyl-5,6,7,8-tetrahydrochinolin (7), das seinerseits aus dem Isomerengemisch der Enamine 8a und 8b erstmals erhalten wird, beschrieben. Der Aufbau von 7 aus 8-Aza-1-tetralon (13) 8a und 8b erstmals erhalten wird, beschrieben. Der Aufbau von 7 uas 8-Aza- 1-tetralon (13) mit geeigneten metallorganischen Reagenzine gelingt dagegen unerwarteterweise nicht.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.197519750606
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  • 2
    Electronic Resource
    Electronic Resource
    Intramolekulare Aromatenalkylierungen, IV. Synthese und Reduktion von N-Methyl-5,6,7,8-tetrahydrochinaldiniumjodid (1976)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1976 (1976), S. 610-616 
    Details
    ISSN: 0075-4617
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Intramolecular Alkylations of Aromatic Compounds, IV.  -  Synthesis and Reduction of N-Methyl-5,6,7,8-tetrahydroquinaldinium iodideThe synthesis of N-methyl-5,6,7,8-tetrahydroquinaldinium iodide (11) from 3-butyn-2-one (5) and 3-amino-2-cyclohexen-1-one (6) via the intermediate 6-methyl-5-aza-1-tetralone (9) is described. Reduction of the title compound11 by sodium borohydride gives the octahydro-and decahydroquinaldine derivatives 12a and 14a. Attempted partial catalytic hydrogenation of 11 does not lead to 12a but to 14a.
    Notes: Es wird die Synthese von N-Methyl-5,6,7,8-tetrahydrochinaldiniumjodid (11) aus 3-Butin-2-on (5) und 3-Amino-2-cyclohexen-1-on (6) über die Zwischenstufe 6-Methyl-5-aza-1-tetralon (9) beschrieben. Die Reduktion der im Titel genannten Verbindung 11 mit Natriumborhydrid liefert die Octahydro- und Decahydrochinaldin-Derivate 12a und 14a. Eine partielle Hydrierung von 11 zu 12a auf katalytischem Wege gelingt nicht; es entsteht vielmehr die perhydrierte Verbindung 14a.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.197619760404
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  • 3
    Electronic Resource
    Electronic Resource
    Intramolekulare Aromatenalkylierungen, I Über die Synthese des 3-Hydroxy-N-methyl-8-aza-des-N-morphinans (1975)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1975 (1975), S. 1065-1069 
    Details
    ISSN: 0075-4617
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Intramolecular Alkylations of Aromatic Compounds. I. - On the Synthesis of 3-Hydroxy-N-methyl-8-aza-de-N-morphinanReduction of teh 5,6,7,8-tetrahydroquinolinium iodides 7a-7c with sodium borhydride gives the corresponding octahydroquinolines 5a-5c. Treatment of 5c with hydrobromic or polyphosphoric acid leads to a cyclic compound, whose structure is not identical with that of the expected compound 6.
    Notes: Die reduktion der 5,6,7,8-Tetrahydrochinoliniumjodide 7a-7c mit Natriumborhydrid fuhrt zu den korrespondierenden Octahydrochinolinen 5a-5c. Bei Behandlung von 5c mit Bromwasserstoff- oder Polyphosphorsäure läβt sich zwar ein Cyclisierungsprodukt isolieren, dessen Struktur jedoch nicht mit der erwarteten Verbindung 6 übereinstimmt.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.197519750604
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  • 4
    Electronic Resource
    Electronic Resource
    Intramolekulare Aromatenalkylierungen, II1) Synthese von 1,2,3,4,4a,5,6,10b-Octahydrobenzo[f]chinolinen (1975)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1975 (1975), S. 1070-1080 
    Details
    ISSN: 0075-4617
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Intramolecular Alkylations of Aromatic Compounds, II1). - Synthesis of 1,2,3,4,4a,5,6,10b-Octahydrobenzo[f]quinloinesSubstituted 2-phenylethyl)pyridinium salts 8 are reduced by sodium borhydride to the corresponding tetrahydropyridine derivatives 9, which can be cyclized to the 1,2,3,4,4a,5,6,10b-Octahydrobenzo[f]quinloines 10.
    Notes: Substituierte 2-(2-Phenyläthyl)pyridiniumsalze 8 lassen sich mit Natriumborhydrid in die korrespondierenden Tetrahydropyridinderivate 9 umwandeln, die zu den 1,2,3,4,4a,5,6,10b-Octahydrobenzo[f]chinoline 10 cyclisiert werden.
    Additional Material: 3 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.197519750605
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  • 5
    Electronic Resource
    Electronic Resource
    Intramolekulare Aromatenalkylierungen, V1) Synthese und Umsetzung von 5,6,7,8-Tetrahydro-8-chinolon (1976)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1976 (1976), S. 1351-1356 
    Details
    ISSN: 0075-4617
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Intramolecular Alkylations of Aromatic Compounds, V 1). - Synthesis and Reaction of 5,6,7,8-Tetrahydro-8-quinolone5,6,7,8-Tetrahydro-S-quinolone (5) is prepared by catalytic hydrogenation of the ozonide 4. The 2-pyridyl ketones Sa-Sd, which have analogous structures to 5, as well as the tetra- hydroquinolone 10 react with phenyllithium in ether to give the expected benzyl alcohols 9a-9d and 11, whereas the corresponding reaction with 5 to give 12 is only successful when 1,2-dimethoxyethane is added as solvent to the reaction mixture.
    Notes: 5,6,7,8-Tetrahydro-S-chinolon (5) ist durch katalytische Hydrierung des Ozonids 4 darstellbar. Die zu 5 strukturanalogen 2-Pyridylketone 8a-8d sowie das Tetrahydrochinolon 10 reagieren mit Phenyllithium in Äther glatt zu den erwarteten Benzylalkoholen 9a-9d bzw. 11, während die entsprechende Umsetzung von 5 zu 12 nur unter Zusatz von 1,2-Dimethoxy- äthan als Lösungsmittel durchführbar ist.
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.197619760723
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  • 6
    Electronic Resource
    Electronic Resource
    Synthese des N-[2-Hydroxy-2-(5-pyrimidinyl)äthyl]phthalimids (1975)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1975 (1975), S. 1252-1256 
    Details
    ISSN: 0075-4617
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Synthesis of N-[2-Hydroxy-2-(5-pyrimidinyl)ethyl]phthalimideStarting from 5-(diazoacetyl)pyrimidine (7) the synthesis of N-[2-Hydroxy-2-(5-pyrimidinyl)ethyl]phthalimide via the intermediates 8→ is described. Attempts to reduce the diazoketone 7 to the aminoalkanol 5 failed.
    Notes: Ausgehend von 5-(Diazoacetyl)pyrimidin (7) wird die Synthese von N-[2-Hydroxy-2-(5-pyrimidinyl)äthyl]phthalimid (10) über die Zwischenstufen 8→9 beschrieben. Die direkte reduktive Umwandlung von 7 zum aminoalkohol 5 gelingt nicht.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.197519750704
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  • 7
    Electronic Resource
    Electronic Resource
    Synthese von cis-3, 10b-Dimethyl-1,2,3,4,4a,5,6,10b-octahydrobenzo[f]isochinolin (1978)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1978 (1978), S. 1963-1967 
    Details
    ISSN: 0075-4617
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Intramolecular Alkylations of Aromatic Compounds, VI.  -  Synthesis of cis-3,10b-Dimethyl-1,2,3,4,4a,5,6,10b-octahydrobenzo[f]isoquinolineThe title compound 4 is stereoselectively formed by intramolecular cyclisation of the tetrahydropyridine derivative 3. which in turn can be prepared via steps 5→10. Reduction of the nitrile 5 with Raney nickel in formic acid immediately yields the aldehyde 6.
    Notes: Die im Titel genannte Verbindung 4 ist stereoselektiv durch intramolekulare Cyclisierung des Tetrahydropyridins 3 darstellbar, das seinerseits über die Stufenfolge 5→10 aufgebaut wird. Der Aldehyd 6 ist durch Reduktion des Nitrils 5 mit Raney-Nickel in Ameisensäure direkt zugänglich.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.197819781210
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