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  • Organic Chemistry  (5)
  • Malononitrile  (2)
  • 1,4-Cyclohexadiene  (1)
  • Aminopyrazoles  (1)
  • 1
    Electronic Resource
    Electronic Resource
    An improved and facile synthesis of 2-amino-1,1,3-tricyanopropene (1985)
    Springer
    Monatshefte für Chemie 116 (1985), S. 689-691 
    Details
    ISSN: 1434-4475
    Keywords: Malononitrile ; Dimerization
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Zusammenfassung Eine einfache Dimerisierung von Malononitril unter Verwendung von Alkalihydroxid in Methanol und Ethanol wird beschrieben. Dabei entsteht in guter Ausbeute 2-Amino-1,1,3-tricyan-propen, ein wichtiges Ausgangsprodukt zur Synthese von Heterocyclen.
    Notes: Abstract A simple method for the dimerization of malononitrile using alkali hydroxides in methanol or ethanol is described. Thereby 2-Amino-1,1,3-tricyanopropene, a keyintermediate for heterocyclic chemistry, is obtained in high yield.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00798796
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  • 2
    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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  • 3
    Electronic Resource
    Electronic Resource
    Synthesen mit Nitrilen, LXXV Zur Reaktivität der Dimeren von Malononitril und Cyanessigester gegenüber Dimethylformamid-dimethylacetal (1987)
    Springer
    Monatshefte für Chemie 118 (1987), S. 617-626 
    Details
    ISSN: 1434-4475
    Keywords: Cyanoacetate ; Dimethylformamide-dimethylacetal ; Malononitrile
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Abstract Reaction of malononitrile dimer (1) and the codimer from cyanoacetate and malononitrile (2) with dimethylformamide-dimethylacetal (DMFDMA) leads to the monocondensation products5 a, b. The isomeric codimer3, however, gives the amidine6. Ring closure reactions of5 a with ammonia and primary aliphatic and aromatic amines yield 2,4-diamino-3,5-pyridinedicarbonitriles7 a–j, in the case of5 b the 4-amino-1,2-dihydro-2-oxo-3,5-pyridinedicarbonitriles8 b–i. Reactions of1 and2 with an excess ofDMFDMA give the biscondensation products11 a, 11 b.11 b reacts with primary aromatic amines to give the pyridine derivatives13. The structure of13 was confirmed by hydrolytical cleavage to the dicyano-aminopyridone14. Treatment of13 with concentrated hydrochloric acid leads to the pyridopyrimidine derivatives15.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00809673
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  • 4
    Electronic Resource
    Electronic Resource
    Synthesen mit Nitrilen, LXXVII. Zur Synthese und Strukturaufklärung von 4-Amino-5-cyan-1-phenyl-3-pyridazincarbonsäure-Derivaten (1987)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1987 (1987), S. 889-892 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Syntheses with Nitriles, LXXVII. - Synthesis and Structure Analysis of 4-Amino-5-cyano-1-phenyl-3-pyridazinecarboxylatesReactions of 3-Amino-4,4-dicyano-3-butenoates (2d, e) with various aryl diazonium salts lead to 4-amino-5-cyano-1,6-dihydro-6-imino-1-phenyl-3-pyridazinecarboxylates 4a-k. In the case of 4a and 4b it is possible to isolate and to characterize the corresponding open-chain intermediates 3a and 3b. Hydrolysis of 4c gives a product, which can be identified by X-ray structure analysis as an inner salt of 4-amino-5-cyano-1,6-dihydro-6-imino-1-phenyl-3-pyridazinecarboxylic acid (5).
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198719870844
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  • 5
    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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  • 6
    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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  • 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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  • 8
    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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