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  • 1
    Electronic Resource
    Electronic Resource
    New syntheses of 2,4-diaminopyrroles and aminopyrrolinones (1997)
    Springer
    Monatshefte für Chemie 128 (1997), S. 933-943 
    Details
    ISSN: 1434-4475
    Keywords: Thorpe-Ziegler cyclization ; (Oxazolin-2-yliden)malononitrile ; 2,4-Diamino-pyrrole ; 2-Amino-4-oxo-pyrrol-3-carbonitrile ; 4-Amino-2-oxo-pyrrol-3-carbonitrile
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Zusammenfassung Die Oxazolin-2-yliden-malononitrile3a–d. die aus Thioketenaminalen und α-Halogenketonen erhalten wurden, reagieren mit primären und sekundären Aminen zu den 2,4-Diaminopyrrolen5a–h. Mercaptobenzol als nukleophiles Reagens liefert 4-Amino-2-phenylthiopyrrol (5j). Analog wurden Cyan-(3,5-diphenyl-3H-oxazol-2-yliden)-essigsäuremethylester als Zwischenprodukte für die Synthese der 2-Amino-4-oxo-pyrroline10a–d hergestellt. Die isomeren 4-Amino-2-oxo-pyrroline13a–d können aus den 4-Amino-2-methoxy-pyrrolen11a,b erhalten werden, was als Nachweis für die Position der Substituenten dient. Die Verbindungen wurden1H- und13C NMR-spektroskopisch untersucht.
    Notes: Summary Oxazolin-2-ylidene-malononitriles3a–d, obtainable from thioketenaminals and α-halogen-ketones, react with primary and secondary amines to afford 2,4-diamino-pyrroles5a–h. Mercaptobenzen as nucleophilic agent gives the 4-amino-2-phenylthio-pyrrole5j. Analogously, cyano-(3,5-diphenyl-3H-oxazol-2-ylidene)-acetic acid methyl esters were prepared as intermediates for the synthesis of 2-amino-4-oxo-pyrrolines10a–d. The isomeric 4-amino-2-oxo-pyrrolines13a–d can be obtained from 4-amino-2-methoxy-pyrroles, which serves as proof for the position of substituents. The structures were investigated by1H and13C NMR spectroscopy.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00807103
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  • 2
    Electronic Resource
    Electronic Resource
    Synthese und Reaktionen von 2-Arylhydrazono-2-cyan-N,N-dialkyl-acetamidinen (1991)
    Springer
    Monatshefte für Chemie 122 (1991), S. 195-207 
    Details
    ISSN: 1434-4475
    Keywords: 5-Dialkylamino-2-aryl-1,2,3-triazoles ; 4-Amino-2,6-dioxo-tetrahydropyrid-3-yl-pyridiniumchloride ; 2-Arylhydrazono-2-cyan-N-chloracetylacetamide ; Arylhydrazono-2-cyan-N,N-dialkylacetamidines ; Arylhydrazonomalononitriles ; 4-Imino-5-arylazo-6-dialkylamino-1,4-dihydropyrimidines ; 13C-NMR
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Summary The title compounds3 were synthesized by reaction of arlyhydrazono-malononitriles1 with secondary amines and used for subsequent cyclization reactions. Thus,3 undergoes cyclooxidation by treatment with CuSO4/pyridine to form the 5-dialkylamino-2-aryl-1,2,3-triazolo-4-carbonitriles4. From4 a and hydrazine hydrate/DMF the 4-(1,3,4-triazolyl-5)-1,2,3-triazole5 c is obtainable. The chloroacetylation of3 is accompanied by hydrolysis of the amino group to yield the arylhydrazono-N-chloracetyl cyanoacetamides6. The quaternisation of6 with pyridins is followed by the Thorpe cyclization to form the 4-amino-5-arylazo-6-hydroxy-3-pyridinio-pyrid-2-on-chlorides8, useful as cationic dyes. The reaction of3 with trichloroacetonitriles yields the 5-arylazo-4-imino-2-trichlormethyl-1,4-dihydropyrimidines10 a–c which can be converted into the 5-arylazo-2-hydrazino-pyrimidine derivatives10 d–f. From10 d the 6-phenylazo-triazolo[4,3-a]pyrimidine derivative11 is obtainable. From3 and phenylisothiocyanate the 5-arylazo-4-imino-1,4-dihydropyrimidin-2-thiones12 arise. The structures were investigated by13C-NMR-spectroscopy.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00809365
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