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  • 1
    Electronic Resource
    Electronic Resource
    2-[N'-(3-Arylallylidene)hydrazino]adenosines Showing A2a Adenosine Agonist Properties and Vasodilation Activity (1995)
    s.l. : American Chemical Society
    Journal of medicinal chemistry 38 (1995), S. 3581-3585 
    Details
    ISSN: 1520-4804
    Source: ACS Legacy Archives
    Topics: Chemistry and Pharmacology
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1021/jm00018a017
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  • 2
    Electronic Resource
    Electronic Resource
    v-Triazolines, XXIV. Pyrazolecarbaldehydes from 5-Amino-4,5-dihydro-4-methylene-v-triazoles and Sydnones (1985)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1985 (1985), S. 1377-1388 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: v-Triazoline, XXIV.- Pyrazolcarbaldehyde aus 5-Amino-4,5-dihydro-4-methylen-v-triazolen und SydnonenDie Sydnone 1a- c ergeben mit den 4,5-Dihydro-v-triazolen 2a- c nach längerem Rückflußerhitzen auf 110- 140°C über nicht isolierbare Primäraddukte nach Eliminierung von CO2 und N2 sowie nach Umlagerung ein Gemisch der 4,5-Dihydropyrazole 3a- c, 3-Pyrazolcarbaldehyd-anile 4a-d und 3-Pyrazolcarbaldehyde 5a-c. Die Verbindungen 3 können zu 4 desaminiert werden, und letztere lassen sich zu 3-Pyrazolcarbaldehyden 5 hydrolysieren.- Die Sydnone 6a, b reagieren ähnlich mit 2a unter Bildung eines Gemisches von 4-Pyrazolcarbaldehyd-anilen 7a, b und 4-Pyrazolcarbaldehyden 8a, b. Die Strukturzuweisungen stützen sich auf spektroskopische Daten und Röntgenstrukturanalysen.
    Notes: The sydnones 1a-c react with the 4,5-dihydro-v-triazoles 2a-c by long refluxing at 110- 140°C affording via non-isolable adducts with elimination of CO2 and N2 and rearrangement a mixture of 4,5-dihydropyrazoles 3a- c, 3-pyrazolecarbaldehyde anils 4a-d, and 3-pyrazolecarbaldehydes 5a-c. Compounds 3 can be deaminated to give 4 which can be hydrolyzed to yield the 3-pyrazolecarbaldehydes 5.- The sydnones 6a, b react similarly with 2a to give a mixture of 4-pyrazolecarbaldehyde anils 7a, b and 4-pyrazolecarbaldehydes 8a, b. The structural assignments are based on spectroscopic and X-ray diffraction data.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198519850709
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  • 3
    Electronic Resource
    Electronic Resource
    v-Triazolines, XXVIII. Reactions of 1-Aryl-4,5-dihydro-4-methylene-5-morpholino-v-triazoles with 2,4-Diaryl-5(4H)-oxazolones (1987)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1987 (1987), S. 1073-1078 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: v-Triazoline, XXVIII. - Reaktionen von 1-Aryl-4,5-dihydro-4-methylen-5-morpholino-v-triazolen mit 2,4-Diaryl-5(4H)-oxazolonen5(4H)-Oxazolone 1a-d mit elektronenliefernden Resten in 2-Position des Arylrests reagieren mit 4,5-Dihydro-v-triazolen 2a-c zu 4-[(4-Triazolyl)methyl]-5-(4H)-oxazolonen 3a-i als Haupt- und zu 2,5-Diaryl-3-pyrrolcarbaldehyden 4a-d sowie Glycindiamiden 5a-d als Nebenprodukten. 5(4H)-Oxazolone mit elektronenziehenden Substituenten (1e-h) liefern mit den 4,5-Dihydro-v-triazolen 2c-e die 2-[(4-Triazolyl)methyl]-5(2H)-oxazolone 7a-e als Hauptprodukte. Die Produkte 3 und 7 werden durch nucleophilen Angriff des Anions von 1 am exo-Methylenkohlenstoff von 2 gebildet. Die Aldehyde 4 entstehen durch Umlagerung eines labilen Cycloaddukts aus 1 und 2.
    Notes: The 5(4H)-oxazolones 1a-d with an electron-rich aryl substituent on C-2 react with 4,5-dihydro-v-triazoles 2a-c to afford the 4-[(4-triazolyl)methyl]-5(4H)-oxazolones 3a-i as main reaction products and 2,5-diaryl-3-pyrrolecarbaldehydes 4a-d and glycine diamides 5a-d as secondary reaction products. The 5(4H)-oxazolones 1e-h bearing an electron-withdrawing substituent on the aryl group on C-2 react with the 4,5-dihydro-v-triazoles 2c-e affording the 2-[(4-triazolyl)methyl]-5(2H-oxazolones 7a-e as main reaction products. Compounds 3 and 7 are produced by nucleophilic attack of the anion of 1 at the exo methylene carbon. Aldehydes 4 are formed through rearrangement of an unstable cycloaddition product from 1 and 2.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198719870875
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  • 4
    Electronic Resource
    Electronic Resource
    4,5-dihydroisoxazoles, IX. Reactions of 3-aryl-4,5-dihydro-4-methylene-5-morpholinoisoxazoles with 2,4-diaryl-5(4H)-oxazolones: A new synthesis of tetrahydro-6-oxo-3-pyridinecarbaldehydes (1990)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1990 (1990), S. 853-855 
    Details
    ISSN: 0170-2041
    Keywords: Isoxazoles ; 5(4H)-Oxazolones ; 3-Pyridinecarbaldehydes, 1,4,5,6-tetrahydro-6-oxo ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The 5(4H)-oxazolones 1a-e react with 5-morpholinoisoxazoles 2a-b to afford the 4-[(4-isoxazolyl)methyl]-5(4H)-oxazolones 3a-g. Compounds 3 are hydrogenated with Pd/C in dioxane to yield the corresponding 1,4,5,6-tetrahydro-6-oxo-3-pyridinecarbaldehydes 6a-d.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.1990199001160
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  • 5
    Electronic Resource
    Electronic Resource
    v-Triazolines - IV:For Part III, see Ref. 1. NMR configuration assignment of 5-dialkylamino-v-triazolines (1972)
    Chichester : Wiley-Blackwell
    Organic Magnetic Resonance 4 (1972), S. 247-251 
    Details
    ISSN: 0030-4921
    Keywords: Chemistry ; Analytical Chemistry and Spectroscopy
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A series of 1-aryl-5-amino-4,5-dihydro-v-triazoles bearing at least one hydrogen atom at the C-4 position has been prepared. The NMR features of the above compounds have been studied with the purpose of differentiating the triazolines with a trans configuration from those with a cis configuration. It has been shown that the hydrogen atom at C-4 lying on the same side of the amine group at C-5 always resonates at lower field than the hydrogen atom on the opposite side. This rule can be applied for identifying the configuration of the 5-amino-v-triazolines.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/mrc.1270040206
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  • 6
    Electronic Resource
    Electronic Resource
    Triazolines, 35. 2-aminoaziridines: Unstable intermediates in thermal decomposition of 5-amino-v-triazolines (1995)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1995 (1995), S. 487-493 
    Details
    ISSN: 0947-3440
    Keywords: v-Triazolines ; Aziridines ; 2-Pyrrolines ; 1-Aza-1,3-dienes ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Pyrolysis of 4-aryl-5-amino-v-triazolines 4 affords two products: benzanilides 5 and acetamidines 6. Pyrolysis of 4 with DMAD under argon produces 1-aza-1,3-dienes 8 and 2-pyrrolines 9. The reaction mechanism of this transformation is discussed. 2-Aminoaziridines are shown to be key intermediates in this reaction.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199519950367
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  • 7
    Electronic Resource
    Electronic Resource
    Versuche im Enamingebiet, XI. Über eine neue, von Säuren ausgelöste Umwandlung einiger Aminotriazoline (1964)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 97 (1964), S. 1225-1231 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Bei den Phenylazid-Addukten des 1-Methyl- und 1-Benzyl-4-morpholino-Δ3-piperideins beobachtet man verschiedene Säurereaktionen. Mit äthanolischer Salzsäure entsteht unter Eliminierung von Morpholin das entsprechende Tetrahydro-pyrido-1.2.3-triazol, während man mit Essigsäure unter Fragmentierung zu 5-[(Methyl- bzw. Benzyl-hydroxymethyl-amino)-äthyl]-1-phenyl-1.2.3-triazol gelangt. Bei Verwendung von Ameisensäure wird die Hydroxymethylgruppe zur Methylgruppe reduziert. Reaktionsmechanismen werden vorgeschlagen.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19640970503
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  • 8
    Electronic Resource
    Electronic Resource
    5-Oxazolones, II. 2,4-Diaryl-4-(2,4-dinitroaryl)-5(4H)-oxazolones: Synthesis and Acid-Catalyzed Transformation into 1-Hydroxy-1H-indazole Derivatives (1988)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 121 (1988), S. 67-73 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: 5-Oxazolone, II. - 2,4-Diaryl-4-(2,4-dinitroaryl)-5(4H)-oxazolone: Synthese und säurekatalysierte Umwandlung in 1-Hydroxy-1H-indazol-Derivate2,4-Diaryl-4-(2,4-dinitroaryl)-5(4H)-oxazolone 2 wurden durch Arylierung der entsprechenden 5(4H)-oxazolone 1 mit 1-Halo-2,4-dinitrobenzol-Derivaten unter Phasentransfer-Bedingungen dargestellt. 2,4-Diaryl-4-(3,5-dinitro-2-pyridyl)-5(4H)-oxazolone 5 wurden ähnlich aus den entsprechenden Derivaten 1 und 2-Chlor-3,5-dinitropyridin erhalten. Durch Reaktion mit Methanol und p-Toluolsulfonsäure lagerten die Oxazolone 2 in die entsprechenden 1-Hydroxy-1H-indazol-Derivate 8 um. Unter denselben Bedingungen lieferten die Oxazolone 5 eine Mischung der entsprechend substituierten 1H-Pyrazolo[4,3-b]pyridine 7 und der substituierten Imidazo[1,5-a]pyridine 12. In allen Fällen trat als Konkurrenzreaktion Solvolyse zu substituierten Glycinestern 9 und 11 auf. Reaktionswege werden diskutiert.
    Notes: 2,4-Diaryl-4-(2,4-dinitroaryl)-5(4H)-oxazolones 2 were prepared by arylation of the corresponding 5(4H)-oxazolones 1 under phase-transfer conditions with the corresponding 1-halo-2,4-dinitrobenzenes. 2,4-Diaryl-4-(3,5-dinitro-2-pyridyl)-5(4H)-oxazolones 5 were obtained similarly from the corresponding 1 and 2-chloro-3,5-dinitropyridine. On reaction with methanol and p-toluenesulfonic acid, oxazolones 2 rearranged to the corresponding 1-hydroxy-1H-indazole derivatives 8. Under the same conditions oxazolones 5 afforded a mixture of the correspondingly substituted 1H-pyrazolo[4,3-b]pyridines 7 and substituted imidazo[1,5-a]pyridines 12. In all cases the solvolysis reaction, yielding substituted glycine esters 9 and 11, was competitive with the rearrangement. Reaction paths are discussed.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19881210111
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  • 9
    Electronic Resource
    Electronic Resource
    v-Triazolines, XXVI. 1,2,5-Trisubstituted 3-pyrrolecarbaldehydes from N-substituted oxazolium-5-olates and 5-amino-4,5-dihydro-4-methylene-v-triazoles (1986)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 119 (1986), S. 1083-1089 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: v-Triazoline, XXVI. 1,2,5-Trisubstituierte 3-Pyrrolcarbaldehyde aus N-substituierten Oxazolium-5-olaten und 5-Amino-4,5-dihydro-4-methylen-v-triazolenDie Cycloaddition von einigen symmetrisch und unsymmetrisch substituierten N-substituierten Oxazolium-5-olaten (2) an 5-Amino-4,5-dihydro-4-methylen-v-triazole (1) wird beschrieben. Durch regiospezifische Cycloaddition entstehen instabile Cycloaddukte, die sofort Kohlendioxid und Stickstoff unter Umlagerung zu 1,2,5-trisubstituierten 3-Pyrrol-carbaldehyd-anilen (3) eliminieren. Die Anile werden leicht zu den entsprechenden 1,2,5-trisubstituierten 3-Pyrrolcarbaldehyden (4) hydrolysiert.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19861190328
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  • 10
    Electronic Resource
    Electronic Resource
    4,5-Dihydroisoxazoles, VII1,2). Rearrangement Reactions of Cycloadducts from 5-Amino-4,5-Dihydro-4-Methyleneisoxazoles and Cyclopentadienones: Synthesis of 2-Azatetracyclo[4.3.0.02,4.03,7]nonane Derivatives (1987)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 120 (1987), S. 1797-1801 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: 4,5-Dihydroisoxazole, VII1,2). - Umlagerung von Cycloaddukten aus 5-Amino-4,5-dihydro-4-methylnisoxazolen und Cyclopentadienonen: Synthese von 2-Azatetracyclo[4.3.0.02,4.03,7]nonan-DerivatenDie Reaktion von 4,5-Dihydro-3-(4-methoxyphenyl)-4-methylen-5-morpholinoisoxazol (1) mit den Cyclopentadienonen 2 lieferte thermisch labile Diels-Alder-Addukte 3. Erhitzen dieser Addukte führt über eine stereokontrollierte Retro-Michael-Reaktion zu einer Mischung der (5-Aminoisoxazolylmethyl)-3- und -2-cyclopenten-1-one 6 und 7. Starkes Erhitzen bewirkt eine Isomerisierung des Isoxazol-Rings von 7 unter Bildung von zwei epimeren Aziridinen. Isoliert werden konnte nur reines 8, das andere Isomere ergab in einer leicht erfolgenden intramolekularen [4+2]-Cycloaddition die entsprechenden 2-Azatetracyclo[4.3.0.02,4.03,7]nonan-Derivate 9.
    Notes: Reaction of 4,5-dihydro-3-(4-methoxyphenyl)-4-methylene-5-morpholinoisoxazole (1) with cyclopentadienones 2 afforded thermally labile Diels-Alder cycloaddition products 3. On heating these products underwent a stereocontrolled retro-Michael process affording a mixture of the corresponding (5-aminoisoxazolyl-methyl)-3- and -2-cyclopenten-1-ones 6 and 7, respectively. At higher temperatures the isoxazole ring of compounds 7 was isomerized to form two epimeric azirines. Only pure 8 was isolated since the other isomer underwent a facile intramolecular [4+2] π-cycloaddition yielding the corresponding 2-azatetracyclo-[4.3.0.02,4.03,7]nonane derivatives 93.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19871201105
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