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  • 1
    Electronic Resource
    Electronic Resource
    Synthese von 4-Aminopyrimidinen aus 1,2,4-Oxadiazolen, I. Eine neue, allgemeine Methode zur Herstellung von 4-Aminochinazolinen und deren Heteroanaloga (1984)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 117 (1984), S. 3183-3193 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Synthesis of 4-Aminopyrimidines from 1,2,4-Oxadiazoles, I. A Novel General Method for the Preparation of 4-Aminoquinazolines and their Hetero AnaloguesCatalytic hydrogenation of 3-(2-aminoaryl)-1,2,4-oxadiazoles (9, 12, 15, 18, 21) to 2-amino-N-acylarenecarboxamidines (10, 13, 16, 19, 22) followed by dehydration gave condensed 4-aminopyrimidines (11, 14, 17, 20, 23), while the corresponding secondary amines (24) afforded 1,2-disubstituted 4-iminoquinazolines (26). Reduction and dehydration of 3-[2-(acylamino)phenyl]-1,2,4-oxadiazoles (28) provided, via a somewhat different pathway, 4-(acylamino)quinazolines (31).
    Notes: Katalytische Hydrierung von 3-(2-Aminoaryl)-1,2,4-oxadiazolen (9, 12, 15, 18, 21) zu 2-Amino-N-acylarencarboxamidinen (10, 13, 16, 19, 22) und nachfolgende Dehydratisierung ergab kondensierte 4-Aminopyrimidine (11, 14, 17, 20, 23), während die entsprechenden sekundären Amine (24) zu 1,2-disubstituierten 4-Iminochinazolinen (26) führten. Reduktion und Dehydratisierung der 3-[2-(Acylamino)phenyl]-1,2,4-oxadiazole 28 lieferte auf einem von dem vorangehenden teilweise verschiedenen Reaktionsweg die 4-(Acylamino)chinazoline 31.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19841171104
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  • 2
    Electronic Resource
    Electronic Resource
    Synthesis of 4-Aminopyrimidines from 1,2,4-Oxadiazoles, II A General Method for the Preparation of 4-Substituted 6,7-Dihydro-9,10-dialkoxy-2H-pyrimido[6,1-a]isoquinolin-2-imine Hydrochlorides (1987)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 120 (1987), S. 1039-1043 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Während die Reduktion von 5′-substituierten 1-[(1,2,4-Oxadiazol-3-yl)methyl]-3,4-dihydroisochinolinen (7) mit NaBH4 selektiv zu den entsprechenden Tetrahydroisochinolinen 8 und durch nachfolgende Ringisomerisierung zu Pyrazolo[5,1-a]isochinolinen 9 führte4), ergab die katalytische Hydrierung von 7 in Anwesenheit von Chlorwasserstoff durch reduktive Spaltung der N-O-Bindung des 1,2,4-Oxadiazolringes und nachfolgende spontane Dehydratisierung ganz allgemein 4-substituierte Pyrimido[6,1a]isochinolin-2-imin-hydrochloride (11).
    Notes: 5′-Substituted 1-[(1,2,4-oxadiazol-3-yl)methyl]-3,4-dihydroisoquinolines (7) were reduced by NaBH4selectively to give the corresponding tetrahydroisoquinolines (8) which underwent ring isomerization to pyrazolo[5,1-a]isoquinolines (9). Catalytic hydrogenation of 7 in the presence of hydrogen chloride, in turn, gave by reductive cleavage of the N-O bond of the 1,2,4-oxadiazole ring and subsequent dehydration, quite generally, 4-substituted pyrimido[6,1-a]isoquinolin-2-imine hydrochlorides (11).
    Additional Material: 6 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19871200625
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  • 3
    Electronic Resource
    Electronic Resource
    Herstellung von Pyrimido[6,1-a]isochinolinen mit Formaldehyd (1981)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 114 (1981), S. 61-66 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Synthesis of Pyrimido[6,1-a]isoquinolines with FormaldehydeThe isoquinolin-1-ylidenacetonitrile derivative 1 reacts with formaldehyde and hydrazine, acylhydrazines or hydroxylamine to give the 3,3′-bi(pyrimidoisoquinoline) 5 and the 3-amino-and 3-hydroxypyrimido[6,1-a]isoquinolines 6 and 8, respectively. 8 was transformed into 12, 14, and 15 which are unsubstituted at N-3 and have various oxidation levels in the pyrimidine moiety.
    Notes: Aus dem Isochinolin-1-ylidenacetonitril 1 wurden mit Formaldehyd und Hydrazin, Acylhydrazinen oder Hydroxylamin das 3,3′-Bi(pyrimidoisochinolin) 5 bzw. die 3-Amino und 3-Hydroxypyrimido[6,1a]isochinolin-Derivate 6 und 8 dargestellt. 8 ließ sich in die an N-3 unsubstituierten Derivate 12, 14 und 15 überführen, die verschiedene Oxidationsgrade im Pyrimidinring aufweisen.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19811140107
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