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  • 1
    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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  • 2
    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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  • 3
    Electronic Resource
    Electronic Resource
    Cycloaddition Reactions of 3-Methyloxazolium-5-olates to 4-Arylidene-5(4H)-isoxazolones (1989)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 122 (1989), S. 295-300 
    Details
    ISSN: 0009-2940
    Keywords: 5(4H)-Isoxazolones, 4-arylidene- ; Münchnones ; Pyrrole-3-carboxylic acids ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Cycloadditions Reaktionen von 3-Methyloxazolium-5-olaten an 4-Aryliden-5(4H)-isoxazoloneDie instabilen Cycloaddukte, die aus den Benzylidenisoxazolen 2 und Oxazolium-5-olaten 1 gebildet werden, erleiden CO2-Eliminierung zu den stereoisomer substituierten 3,7-Diazaspiro-[4,4]nonan-Derivaten 3, die in einem Fall (3a, b) isoliert wurden. Durch weitere Reaktionen werden die Verbindungen 3 in die Pyrrol-3-carbonsäuren 4 übergeführt. Reaktionswege und regiochemisches Verhalten werden diskutiert.
    Notes: The unstable cycloadducts formed from benzylideneisoxazolones 2 and oxazolium-5-olates 1 undergo CO2 elimination to afford the stereoisomeric substituted 3,7-diazaspiro[4,4]nonane derivatives 3, which were isolated in one case (3a, b). On further reaction, compounds 3 are transformed into pyrrole-3-carboxylic acids 4. Reaction paths and regiochemical behaviour are discussed.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19891220215
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  • 4
    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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  • 5
    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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  • 6
    Electronic Resource
    Electronic Resource
    Triazolines, XXXI[1] Reaction of 5-Amino-4,5-dihydro-4-methylene-1H-1,2,3-triazoles with Substituted Thiazolium-4-olates (1992)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 125 (1992), S. 883-887 
    Details
    ISSN: 0009-2940
    Keywords: v-Triazolines ; Thiazolium-4-olates ; 2-Pyridinones ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The cycloaddition reaction of 5-amino-v-triazolines 2 with thiazolium-4-olates 1 affords two isomeric cycloadducts 3 and 4. A synthetic utilization has been achieved by their desulfuration: The cycloadducts 3 and 4 are catalytically transformed with Raney nickel to pyridinones 5. The acid-catalized rearrangement of 3 and 4 affords the 8-thia-6-azabicyclo[3.2.1]-octane derivatives 6.
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19921250419
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