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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
    Cyclisierungen mit 1-Nitro-2-anilino-äthylenen (1977)
    New York, NY : Wiley-Blackwell
    Journal für Praktische Chemie/Chemiker-Zeitung 319 (1977), S. 149-158 
    Details
    ISSN: 0021-8383
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Cyclizations with 1-nitro-2-anilino-ethylenesThe reaction of 1-nitro-2-anilino-2-methylthio-ethylenes 1 with oxalyl chloride yields the substituted 4-nitropyrrol-2,3-diones 4, and with chlorocarbonyl-sulfenylchloride the 5-nitro-thiazolones 6. The methylthio group from 6 can be exchanged by amines. From 1-nitro-2,2-bis(anilino)ethylenes 2 - available from 1-nitro-2,2-bis(methylthio)-ethylene and anilines - and the same reagents, the substituted 2-nitromethylene-imidazolidine-4,5-diones 5 and the thiazolo[4,5-d]thiazoledione 9 result. The condensation of 1-nitro-2-anilino-2-hydrazino-ethylene 3 with derivatives of carboxylic acids yields 2-nitromethyl-s-triazole 12, with diacetyl the substituted 3-nitromethylene-as-triazine 13.
    Notes: 1-Nitro-2-anilino-2-methylmercapto-äthylen 1 reagiert mit Oxalylchlorid zu substituierten 4-Nitropyrroldionen-(2,3) 4 und mit Chlorcarbonyl-sulfenylchlorid zu substituierten 5-Nitrothiazolonen-(2) 6, deren Methylmercaptogruppe gegen Amine austauschbar ist. 1-Nitro-2,2-bis(anilino)-äthylene 2 - erhältlich aus 1-Nitro-2,2-bis(methylmercapto)-äthylen und Anilinen  -  liefert mit den gleichen Agenzien substituierte 2-Nitromethylenimidazolidindione-(4,5) 5 und das Thiazolo[4,5-d]thiazoldion 9. 1-Nitro-2-anilino-2-hydrazino-äthylen 3 wird mit Carbonsäurederivaten zu substituierten 2-Nitromethyl-s-triazolen 12, mit Diacetyl zum 3-Nitromethylen-as-triazin derivat 13 kondensiert.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/prac.19773190120
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  • 3
    Electronic Resource
    Electronic Resource
    3-Amino-5-nitromethylen-1,2-dithiol-4-carbonsäureester (1981)
    New York, NY : Wiley-Blackwell
    Journal für Praktische Chemie/Chemiker-Zeitung 323 (1981), S. 133-136 
    Details
    ISSN: 0021-8383
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Methyl(3-amino-5-nitromethylene-1,2-dithiol-4)carboxylate
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/prac.19813230119
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  • 4
    Electronic Resource
    Electronic Resource
    Einstufige Synthese von Pyrazino[1,2-a:4,5-a′]diindol-6,13-dionen (1987)
    New York, NY : Wiley-Blackwell
    Journal für Praktische Chemie/Chemiker-Zeitung 329 (1987), S. 745-748 
    Details
    ISSN: 0021-8383
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/prac.19873290428
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  • 5
    Electronic Resource
    Electronic Resource
    Zur Chemie der 5-Amino-2-phenyl-1,2,3-thiadiazoliumsalzeHerrn Prof. Dr. R. Mayer zum 60. Geburtstag gewidmet (1986)
    New York, NY : Wiley-Blackwell
    Journal für Praktische Chemie/Chemiker-Zeitung 328 (1986), S. 741-749 
    Details
    ISSN: 0021-8383
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: On the Chemistry of 5-Amino-2-phenyl-1,2,3-thiadiazolium SaltsTreatment of the title compounds 1 with pyridine yield the phenylhydrazones of the 1,2,4-thiadiazol-3,5-diyl-glyoxylic acid derivatives 4. The amides 4a, b can also be obtained by reaction of the phenylhydrazono cyanacetoamides 3a, b with sulphur in the presence of pyridine. Nitriles react with 1 to form the phenylhydrazones of the 1,2,4-thiadiazol-5-yl-glyoxylic acid derivatives 6. Reduction of 6a yields the 1,2,4-thiadiazol-5-yl-glycine derivative 7. Depending on its condition the reaction of 1c with benzoyl acetonitrile yield either the 1,2,4-thiadiazole or the 4-amino-thiazole derivative (6i or 8). From 1a and ethyl acetoacetate the phenylhydrazone of the thiazol-2-yl-glyoxylic acid derivative 9 arises which can be reduced to yield the thiazol-2-yl-glycine derivative 10. The addition of 1 onto isothiocyanates in the presence of pyridine yields the substituted N-(1,2,3-thiadiazol-5-ylidene)-thioureas 12a, b. Carboxylic acids react with 1 in the presence of pyridine to form the 5-Acylimino-1,2,3-Δ3-thiadiazolines 13.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/prac.19863280512
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  • 6
    Electronic Resource
    Electronic Resource
    5-Arylamino-3-brom-1,2,4-thiadiazole und 5-Arylamino-3-bromisothiazole (1987)
    New York, NY : Wiley-Blackwell
    Journal für Praktische Chemie/Chemiker-Zeitung 329 (1987), S. 355-358 
    Details
    ISSN: 0021-8383
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: 5-Arylamino-3-bromo-1,2,4-thiadiazoles and 5-Arylamino-3-bromo-isothiazoles
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/prac.19873290230
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  • 7
    Electronic Resource
    Electronic Resource
    Reaktion von methylenaktiven Nitrilen und Cyanamid mit acylierten Enaminen (1982)
    New York, NY : Wiley-Blackwell
    Journal für Praktische Chemie/Chemiker-Zeitung 324 (1982), S. 933-941 
    Details
    ISSN: 0021-8383
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Reaction of Methylene Active Nitriles and Cyanamide with Acylated EnaminesThe addition products from enamines onto isocyanates and isothiocyanates, i.e. substituted β-aminoacrylo amides 1 and thioamides 2, react with malononitrile to yield the 6-amino-1-aryl-5-cyano-pyridin-2-ones 3 and -thiones 4 among them 5,6,7,8-tetrahydroisoquinolin-1-ones and -thiones. From ethyl cyanoacetate the 5-cyano-6-hydroxy-pyridin-2-ones 7 and from benzoyl acetonitrile the 6-phenyl-pyridin-2-ones 8 are formed. The replacement of malononitrile by cyanamide yields the 2-amino-3-aryl-pyrimidin-4-ones 5 and -thiones 6 among them 5,6,7,8-tetrahydroquinazolin-4-ones and -thiones. The not isolated β-acyl enamines derived from enamines and acid chlorides react with malononitrile or cyanamide to form the pyridin-2-ones 14 or pyrimidin-2-ones 15 caused by Dimroth-rearrangement.
    Additional Material: 3 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/prac.19823240611
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  • 8
    Electronic Resource
    Electronic Resource
    Zur Reaktion von 1, 1-Dimethylthio- und 1-Dimethylamino-2-nitroethen mit dimerem Malononitril (1985)
    New York, NY : Wiley-Blackwell
    Journal für Praktische Chemie/Chemiker-Zeitung 327 (1985), S. 328-332 
    Details
    ISSN: 0021-8383
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Reaction of 1, 1-Dimethylthio- and 1-Dimethylamino-2-nitroethene with Malononitrile Dimer
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/prac.19853270218
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  • 9
    Electronic Resource
    Electronic Resource
    3-Amino-thieno[2,3-b]furane und 3-Amino-thieno[3,2-b]furane (1983)
    New York, NY : Wiley-Blackwell
    Journal für Praktische Chemie/Chemiker-Zeitung 325 (1983), S. 457-462 
    Details
    ISSN: 0021-8383
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: 3-Amino-thieno[2,3-b]furans and 3-Amino-thieno[3,2-b]furansThe O-alkylation of 2-hydroxy-thiophene-3-carbonitriles (1) with α-bromocarbonyl compounds yields the 2-alkoxy-thiophene-3-carbonitriles (2a-f) among them 2-benzoylmethoxy-thiophene-3-carbonitriles (2a-c) which undergo Thorpe-Ziegler-cyclization to form the 3-amino-2-benzoyl-thieno[2,3-b]furans (3) in low yields. The 2-acyl-3-amino-thieno[3,2-b]furans and ethyl 3-amino-thieno[3,2-b]furan-2-carboxylates (6) are synthesized in similar manner from 3-hydroxy-thiophene-2-carbonitriles (4) and α-halogencarbonyl compounds via 3-acylmethoxy- and 3-ethoxycarbonylmethoxy-thiophene-2-carbonitriles (5) with high yields.
    Additional Material: 3 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/prac.19833250315
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  • 10
    Electronic Resource
    Electronic Resource
    Substituierte 3,4-Diamino-thieno[2,3-b]pyrrole (1986)
    New York, NY : Wiley-Blackwell
    Journal für Praktische Chemie/Chemiker-Zeitung 328 (1986), S. 459-464 
    Details
    ISSN: 0021-8383
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Substituted 3,4-Diamino-thieno[2,3-b]pyrroles
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/prac.19863280325
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