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  • 1
    Electronic Resource
    Electronic Resource
    Ein Beitrag zur Chemie des 2,3-Dihydro-3-oxo-benzo[b]thiophen-1,1-dioxids Synthesen mit Nitrilen, 86. Mitt. (1990)
    Springer
    Monatshefte für Chemie 121 (1990), S. 299-309 
    Details
    ISSN: 1434-4475
    Keywords: 3-Dicyanomethylene-2,3-dihydro-benzo[b]thiophene-1,1-dioxide ; Benzo[b]thieno[2,3-d]thiophene-8,8-dioxide ; Benzo[4,5]thieno[2,3-c]pyridazine-9,9-dioxide ; 1,2-Dihydro-1-oxo-1H-benzo[4,5]thieno[2,3-c]pyridine-9,9-dioxide ; Benzo[4,5]thieno[2,3-c]pyridine-9,9-dioxide
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Summary 2,3-Dihydro-3-oxo-benzo[b]thiophen-1,1-dioxide (1) reacts as CH-acidic component with amidines of orthoesters and anilines resp. to give the anilinomethylene derivates3, 4, and5. With triethyl orthoformiate the hydroxymethylene-compound7 is obtained. Anilino- and phenylhydrazino derivates8 and9 prove the carbonyl activity of1, azo-coupling leads to10, whereas treatment of1 with sulfur and malononitrile yields the benzo[b]thieno[2,3-d]thiophenes11. Introduction of substituents with active NH-functions in position 2 of the dicyanomethylene-product2, such as azocoupling, reaction with phenyl isocyanate and formation of enamines, leads to ring closure reactions between a nitrile and the NH-group. Thereby the phenyl-benzo[4,5]thieno[2,3-c]pyridazines12, the phenyl-1H-benzo[4,5]thieno[2,3-c]pyridines13 and the phenylamino-benzo[4,5]thieno[2,3-c]pyridines14 are obtained.13C and15N-NMR spectroscopy was used as proof of the ring closure reactions.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00808932
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  • 2
    Electronic Resource
    Electronic Resource
    Diphenyldiaza-18-krone-6-bis-pyrazoliden-acetonitril, ein neuer Chromoionophor Synthesen mit Nitrilen, 90.Mitt. (1992)
    Springer
    Monatshefte für Chemie 123 (1992), S. 581-585 
    Details
    ISSN: 1434-4475
    Keywords: 7,16-Diphenyl-1,4,10,13-tetraxoxa-7,16-diaza-cyclooctadecan ; Dicyanomethylene-pyrazolinone ; Chromoionophores by thermolysis or photolysis ; Complex formation constants
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Summary An improved synthesis of 7,16-diphenyl-1,4,10,13-tetraoxa-7,16-diaza-cyclooctadecan (5) is presented and the reaction with 4-dicyanomethylene-3-methyl-1-phenyl-2-pyrazolin-5-on to the colorless adduct6 described. By heating or photolysis6 can be converted to the deeply colored polymethine7. Complex formation constants with potassium ion by1H-NMR-measurements have been determined.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00816852
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  • 3
    Electronic Resource
    Electronic Resource
    Cyanoacetaldehyde — New synthetic applications of an old compound syntheses with nitriles, XCI (1993)
    Springer
    Monatshefte für Chemie 124 (1993), S. 199-207 
    Details
    ISSN: 1434-4475
    Keywords: Cyanoacetaldehyde ; Hydrazones ; Cyanopyrazoles ; Aminopyrazoles
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Zusammenfassung Verschiedene Umsetzungen mit Cyanacetaldehyd (1), welcher durch Ozonolyse von (E)-1,4-Dicyanbuten oder Allylcyanid hergestellt wurde, werden beschrieben. Reaktion von1 mit Anilinen führt zu den β-Phenylaminoacrylnitrilen2a–e. Umsetzungen von1 mit Hydrazinen ergeben die entsprechenden Hydrazonderivate3a–e, welche unter alkalischen Bedingungen zu den 5-Aminopyrazolen4a–d cyclisiert werden können. Ein Aldol-ähnliches Kondensationsprodukt5a wird durch Reaktion von1 mit Natriumphenolat erhalten. Erhitzen von1 in Dimethylformamiddimethylacetal führt zur Bildung von (E)-3-Dimethylamino-2-formylpropennitril (6), ein wichtiges Zwischenprodukt für organische Synthesen. Die Struktur kann mit NOE-Experimenten geklärt werden. Reaktion von6 mit Hydrazinen führt zu 1-substituierten 4-Cyanpyrazolen7a–k.
    Notes: Summary Various reactions of cyanoacetaldehyde (1), freshly prepared by ozonization of (E)-1,4-dicyano-2-butene or allylcyanide, are described. Thus, conversion of1 with anilines gave β-phenylaminoacrylonitriles2a–e. Reaction of1 with hydrazines led to the corresponding hydrazones3a–e, which could be cyclized under alkaline conditions to 5-aminopyrazoles4a–d. An aldol-type condensation product5a could be obtained by reaction of1 with sodiumphenoxide. Treatment of1 with dimethylformamide-dimethylacetal led to the formation of (E)-3-dimethylamino-2-formylpropenenitrile (6), a very useful synthon in synthetic chemistry. For the determination of the structure of6 the method of steady state differential NOEs was used. Reaction of6 with hydrazines gave 1-substituted-4-cyanopyrazoles7a–k.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00808679
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  • 4
    Electronic Resource
    Electronic Resource
    Synthesen mit Nitrilen, 85. Mitt.: Über 4-Dicyanmethylen-und 4-Tricyanpropyliden-homophthalimide (1990)
    Springer
    Monatshefte für Chemie 121 (1990), S. 189-193 
    Details
    ISSN: 1434-4475
    Keywords: Cyanomethylene compounds ; Retro Michael addition ; Tetracyanoethylene
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Summary Addition of tetracyanoethylene to the 1,2,3,4-tetrahydro-isoquinoline-1,3-diones1 a–d yields 4-(dicyanomethylene)-1,2,3,4-tetrahydro-isoquinoline-1,3-diones3 or 4-(2-amino-1,1,3-tricyano-3-propylidene)-1,2,3,4-tetrahydro-1,3-diones4 depending on the substituent in position 2. Spectra of both types of derivatives are discussed.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00809531
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  • 5
    Electronic Resource
    Electronic Resource
    Synthesen mit Nitrilen, LXXXVII. Chromoionophore durch Addition von N-Phenyl(aza-15-krone-5) an reaktive Dicyanmethylenverbindungen (1990)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1990 (1990), S. 741-744 
    Details
    ISSN: 0170-2041
    Keywords: Chromoionophores, complex formation constants ; Polymethine dyes ; Dicyanomethylene compounds ; Crown ether derivatives ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Syntheses with Nitriles, LXXXVII.  -  Chromoinophores by Addition of N-Phenyl(aza-15-crown-5) to Reactive Dicyanomethylene CompoundsAddition of N-phenyl(aza-15-crown-5) (2) to dicyanomethylene compounds, i.e. the pyrazolylidenemalonitriles 1a-e, leads to the colorless (azacrownphenyl)(pyrazolyl)malonitriles 3a-e. Heating or photolysis of 3 eliminates hydrocyanic acid to give the deeply colored polymethines 4a-e. A corresponding reaction occurs between the indanylidenemalonitrile 5 and the crown ether 2 leading to adduct 6, which can be converted into the polymethine 7 by heating or photolysis. For evaluation of constants of the complex formation with sodium or potassium ions 1H NMR chemical shift measurements have been performed.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.1990199001139
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  • 6
    Electronic Resource
    Electronic Resource
    Syntheses with Nitriles, IXC. Preparation, Structure, and Color of 4-[(Cyano)indolylmethylene]- and 4-[(Cyano)pyrrolylmethylene]-1H-pyrazol-5(4H)-ones (1992)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1992 (1992), S. 7-14 
    Details
    ISSN: 0170-2041
    Keywords: Calculations, AM1 and INDO, S-CI ; Cyanomethylene compounds ; Pyrazolones ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: (Dicyanomethylene)pyrazolones 1a, b are treated with some indoles and pyrroles. The resulting disubstituted malono-nitriles 2a-f, 4a-e, 6 yield cyanomethylene compounds 3a-f, 5a-e, 7 by irreversible thermal or photochemical decomposition. The compounds exist in different isomeric forms. Structures are proven by NMR spectroscopy and X-ray analysis. UV-Vis data are discussed by means of AM1 and INDO/S-CI calculations.
    Additional Material: 4 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199219920103
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  • 7
    Electronic Resource
    Electronic Resource
    Ozonolyse von Olefinen, I. Ozonolyse von 1,4-Cyclohexadien und säurekatalysierte Folgereaktionen von Primärspaltprodukten (1990)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1990 (1990), S. 185-188 
    Details
    ISSN: 0170-2041
    Keywords: Ozonolysis ; 1,4-Cyclohexadiene ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Ozonolysis of Olefins, I.  -  Ozonolysis of 1,4-Cyclohexadiene and Acid-Catalysed Reaction of Primary Cleavage ProductsThe reaction of 1,4-cyclohexadiene (1) with ozone under different reaction conditions was investigated. Complete ozonolysis of 1 in chloroform led to a highly explosive ozonide. Oxidative ozonolysis gave malonic acid in 30% yield, ozonolysis in alcoholic solutions of HCl gave alkyl 3,3-dialkoxypropionates 3 in 60-70% yield and small amounts of the 1,1,3,3-tetraalkoxypropane 4 as well as dialkyl malonate 5. Partial ozonolysis of 1 in HCl/methanol led to a mixture of 3, 5, and the corresponding (Z)-3-hexene derivatives 6a-c. Depending on the reaction time and concentration of HCl, also the two methanol addition products 7b and 7d could be obtained. To verify the structure of these two compounds, 4-methoxycyclohexene (8) was ozonized in HCl/methanol, which gave a mixture of 7a-d.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199019900131
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