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  • 1
    Electronic Resource
    Electronic Resource
    (N-Phenyl-aza-Krone)-ethenyl-acridine - Komplexbildende Chromoionophore und Vorstufen für tiefblau gefärbte Hemicyanine (1997)
    New York, NY : Wiley-Blackwell
    Journal für Praktische Chemie/Chemiker-Zeitung 339 (1997), S. 742-745 
    Details
    ISSN: 0941-1216
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: (N-Phenyl-aza-crown)-ethenyl-acridines - Complexing Chromoionophores and Precursors for Deep Blue Coloured HemicyaninesAromatic aldehyde derivatives of N-phenyl-aza-15-crown-5 and N-phenyl-aza-18-crown-6 (1a-b) are condensed with 9-methylacridine to give yellow phenyl-ethenylacridine derivatives 3a-b which are reversibly converted by protonation into deep blue colored hemicyanines, Using 9,10-dimethylacridinium perchlorate in the condensation with the crown ether aldehyde 1 the blue hemicyanine 6 is directly obtained. UV/VIS absorption spectra of the basic/acidic forms of the acridine derivatives are presented. The complex formation of the crown ether derivatives with Na+ and K+ are studied using 1H-NMR and UV/VIS spectroscopy.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/prac.199733901134
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  • 2
    Electronic Resource
    Electronic Resource
    Synthesen mit Nitrilen, LVI. Neue einfache Synthese von 4-Aminosalicylsäure- und Isophthalsäurederivaten (1979)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1979 (1979), S. 2005-2010 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Syntheses with Nitriles, LVI.  -  A Novel Facile Synthesis of 4-Aminosalicylic Acid and Isophthalic Acid DerivativesTreatment of malonodinitrile with triethyl orthoformate affords ethoxymethylenemalonodinitrile, which reacts with alkyl β-oxocarboxylates to yield the substituted 4-aminosalicylates 4a - c. Acid or basic hydrolysis of the nitrile and ester groups of 4a - c leads to the new derivatives 5a, 7a - c, 8a - c, and 9a of 4-aminosalicylic acid. The isophthalic acid derivatives 6a - c are obtained by basic hydrolysis of 4a - c.
    Notes: Aus Malonsäuredinitril und Orthoameisensäure-triethylester erhält man Ethoxymethylenmalonsäuredinitril, welches mit β-Oxocarbonsäureestern zu den substituierten 4-Aminosalicylsäure-estern 4a - c reagiert. Durch saure oder alkalische Hydrolyse der Nitril- und Estergruppen von 4a - c entstehen die neuen Derivate 5a, 7a - c, 8a - c und 9a der 4-Aminosalicyclsäure; allein durch alkalische Hydrolyse erhält man die Isophthalsäurederivate 6a - e.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.197919791210
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  • 3
    Electronic Resource
    Electronic Resource
    Synthesen mit Nitrilen, LXVIII. 4-Dicyanmethylen-1,4-dihydropyrimidine und Pyrido[4,3-d]-pyrimidin-8-carbonitrile aus Enaminonitrilen (1983)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1983 (1983), S. 1107-1115 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Syntheses with Nitriles, LXVIII. - 4-Dicyanomethylene-1,4-Dihydropyrimidines and Pyrido [4,3-d]pyrimidine-8-carbonitriles from EnaminonitrilesReaction of “dimeric malononitrile” (1a) or 3-amino-2-cyano-crotononitrile (1b) with dimethyl-formamide dimethyl acetal gives the biscondensation products 2. Subsequent treatment of 2a with ammonia and 2b with primary aliphatic amines leads to 4-dicyanomethylene-1,4-dihydropyrimidines 3. There are several possible structures for the reaction products obtained from 2a and primary aliphatic and aromatic amines. The structure of the product from 2a and propylamine is confirmed by X-ray structure analysis as 5,6-dihydro-5-imino-6-propyl-4-(propylamino)pyrido[4,3-d] pyrimidine-8-carbonitrile (4c). Hydrolysis of 4 in acidic medium leads to the 5-oxo derivatives 5.
    Notes: Reaktion von “dimerem Malononitril” (1a) oder 3-Amino-2-cyancrotonsäurenitril (1b) mit Dimethylformamid-dimethylacetal ergibt die Biskondensationsprodukte 2. Die Umsetzung von 2a mit Ammoniak oder 2b mit primären aliphatischen Aminen führt zu 4-Dicyanmethylen-1,4-dihydropyrimidinen 3. Für die Reaktionsprodukte aus 2a mit primären aliphatischen und aromatischen Aminen sind mehrere isomere Strukturen möglich. Die Röntgenstrukturanalyse des Produktes von 2a mit Propylamin sichert die Struktur eines 5,6-Dihydro-5-imino-6-propyl-4-(propylamino)pyrido[4,3-d]pyrimidin-8-carbonitrils (4c). Saure Hydrolyse von 4 liefert die 5-Oxo-Derivate 5.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198319830704
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  • 4
    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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  • 5
    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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  • 6
    Electronic Resource
    Electronic Resource
    Synthesen mit Nitrilen, LXVI Synthese des 1,2,3,4-Tetrachlorpentafulven-6,6-dicarbonitrils (1983)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1983 (1983), S. 154-158 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: 1,2,3,4-Tetrachloropentafulvene-6,6-dicarbonitrile (2) is obtained by the reaction of 1,2,3,4-tetrachloro-1,3-cyclopentadiene (1) with ethylenetetracarbonitrile by partial retro-Michael addition. The electronic and 13C NMR spectra are discussed.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198319830116
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  • 7
    Electronic Resource
    Electronic Resource
    Synthesen mit Nitrilen, LXVII. (Ethoxymethylen)malononitril als Synthon zur Darstellung pyrano- und pyridokondensierter Heterocyclen (1983)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1983 (1983), S. 695-704 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Syntheses with Nitriles, LXVII. - (Ethoxymethylene)malononitrile as Synthon for the Preparation of Fused Heterocyclic Pyrano and Pyrido Systems(Ethoxymethylene)malononitrile (2) reacts with 4-hydroxy-2-quinolones 1a, b to give the pyranoquinolines 3a-c. With 4-hydroxycoumarin (4b) or its sodium salt 4a, dependent on the reaction conditions, the [1]benzopyranopyridines 6a, b or the pyrano[1]benzopyran 5a, respectively, are obtained. The carboxylic acid 7 is prepared by basic hydrolysis of 6a, dealkylated to give 8b by treatment with sulfuric acid, and after decarboxylation the [1]benzopyrano[4,3-b]pyridine 9 can be obtained. 4-Hydroxy-6-methyl-2H-pyran-2-one reacts with 2 to give the pyrano[4,3-b]pyran derivative 10. Reaction of 1,3-cyclohexanediones with 2 affords the 5,6,7,8-tetrahydro[1]benzopyrans 11a-c. The fluorescent properties of 3, 5, 8a, 10, and 11 are discussed.
    Notes: (Ethoxymethylen)malononitril (2) reagiert mit den 4-Hydroxycarbostyrilen 1a, b zu den Pyranochinolinen 3a-c, mit 4-Hydroxycumarin (4b) oder dessen Natriumsalz 4a je nach Reaktionsbedingungen zu den [1]Benzopyranopyridinen 6a, b bzw. zum Pyrano[1]benzopyran 5a. Durch alkalische Hydrolyse von 6a entsteht die Carbonsäure 7, die mit konzentrierter Schwefelsäure zu 8b desalkyliert und schließlich zum [1]Benzopyrano[4,3-b]pyridin 9 decarboxyliert werden kann. Mit 4-Hydroxy-6-methyl-2H-pyran-2-on ergibt 2 das Pyrano[4,3-b]pyranderivat 10. Aus der Reaktion von 2 mit 1,3-Cyclohexandionen gehen die 5,6,7,8-Tetrahydro[1]benzopyrane 11a-c hervor. Die Fluoreszenzeigenschaften der Verbindungen 3, 5, 8a, 10 und 11 werden verglichen.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198319830419
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  • 8
    Electronic Resource
    Electronic Resource
    Synthesen mit Nitrilen, LXXVIII. Untersuchungen zur Struktur der Dimeren des Malononitrils, Cyanessigesters und Cyanacetamids (1987)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1987 (1987), S. 1131-1132 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Syntheses with Nitriles, LXXVIII. - Studies on the Structure of Dimers of Malononitrile, Cyanoacetate, and CyanoacetamideThe 13C- and 15N-NMR data of dimers and codimers of malononitrile, cyanoacetate, and cyanoacetamide 1-6 are discussed In the case of the unsymmetrically substituted derivatives 2, 4 and 5 it is possible to distinguish between E- and the predominantly existing Z-isomers. In the case of 2 the structure is confirmed by X-ray structure analysis.
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198719870888
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  • 9
    Electronic Resource
    Electronic Resource
    Notiz über die Reaktion von Carbonsäurehalogeniden mit Ninhydrin (1980)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1980 (1980), S. 1919-1922 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Note on the Reaction of Acyl Halides with NinhydrinAcyl chlorides and bromides readily react with ninhydrin to give the 2-halo-1,3-dioxo-2-indanyl-carboxylates 1a-c. In the presence of small amounts of dimethylformamide, thionyl chloride reacts with ninhydrin to furnish 2,2-dichloro-1,3-indandione (2). Reaction of 1a with pyrrolidine leads to 1-oxo-2-(1-pyrrolin-1-ylio)-1H-indenolate (3).
    Notes: Carbonsäurechloride und -bromide reagieren leicht mit Ninhydrin zu den (2-Halogen-1,3-dioxo-2-indanyl)carboxylaten 1a-c. Thionylchlorid setzt sich mit Ninhydrin bei Anwesenheit kleiner Mengen Dimethylformamid zu 2,2-Dichlor-1,3-indandion (2) um. Die Reaktion von 1a mit Pyrrolidin ergibt 1-Oxo-2-(1-pyrrolin-1-ylio)-1H-inden-3-olat (3).
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198019801131
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  • 10
    Electronic Resource
    Electronic Resource
    Synthesen mit Nitrilen, LXXIV. 3-Amino-4,4-dicyan-3-butensäureester, ein Synthesebaustein aus der Reihe der Dimeren von Malononitril und Cyanessigester (1986)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1986 (1986), S. 533-544 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Syntheses with Nitriles, LXXIV.  -  3-Amino-4,4-dicyano-3-butenoate, a Synthetically Useful Dimer from Malononitrile and CyanoacetateAn improved synthesis of 3-amino-4,4-dicyano-3-butenoate (4) (a codimer from cyanoacetate and malononitrile) is described. The 13C NMR data and pKa value of 4 are compared with those of the isomeric codimer 3 and the dimers 1 and 2. Reaction of 4 with acids or bases leads to the 2(1H)-pyridones 8 and 9, respectively. Conversions of 4 with aldehydes, ketones, and nitroso compounds give the products 11, 14, and 15 as well as the benzopyran derivatives 12 and the 2-oxochinoline derivative 13 when using 2-hydroxy- and 2-aminobenzadehydes. 4 reacts with formamidine to yield the dihydropyrimidine derivative 17 and with sulfur to give the 3,5-diamino-4-cyano-2-thiophenecarboxylates (18).
    Notes: Für die 3-Amino-4,4-dicyan-3-butensäureester (4) (Codimeres aus Cyanessigester und Malononitril) wird eine verbesserte Synthese beschrieben. Die 13C-NMR-Daten und der pKs-Wert von 4 werden mit denen des isomeren Codimeren 3 sowie der Dimeren 1 und 2 verglichen. Reaktion von 4 mit Säuren oder Basen führt zu den 2(1H)-Pyridonen 8 bzw. 9. Umsetzungen von 4 mit Aldehyden, Ketonen und Nitrosoverbindungen liefern die Produkte 11, 14 und 15, wobei mit 2-Hydroxy- und 2-Aminobenzaldehyden die Benzopyranderivate 12 bzw. das 2-Oxochinolinderivat 13 entstehen. 4 liefert mit Formamidin das Dihydropyrimidinderivat 17 und mit Schwefel die 3,5-Diamino-4-cyan-2-thiophencarbonsäureester (18).
    Additional Material: 5 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198619860311
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