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  • 1
    Electronic Resource
    Electronic Resource
    New York, NY : Wiley-Blackwell
    Journal für Praktische Chemie/Chemiker-Zeitung 336 (1994), S. 628-631 
    ISSN: 0941-1216
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
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  • 2
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: 1,2,4-Oxadiazoles containing a C-5-heteroatom Bond, II Synthesis of 5,6-Dihydro-4H-1,2,4-Oxadiazines by ring Extention of Δ2-1,2,4-oxadiazolin-5-onesN-(2-Hydroxyalkyl)-, and N-(3-chloro-2-hydroxypropyl)-Δ2-1,2,4-oxadiazolin-5-one derivatives (6, 8), prepared by reaction of Δ2-1,2,4-oxadiazolin-5-ones (4) with alkylene oxides or epichlorohydrine, respectively, are used as starting materials for the synthesis of 5,6-dihydro-4H-1,2,4-oxadiazines (2) as well as for that of N-monosubstituted amidoximes (7, 11). The reactivity of 2 with methyl iodide and acylating agents is reported.
    Notes: Die durch Reaktion der Δ2-1,2,4-Oxadiazolin-5-one 4 mit Epoxiden bzw. Epichlorhydrin hergestellten N-(2-Hydroxyalkyl)- bzw. N-(3-Chlor-2-hydroxypropyl)-Derivate 6, 8 werden bei der Synthese von 5,6-Dihydro-4H-1,2,4-oxadiazinen (2) bzw. der N-monosubstituierten Amidoxime 7, 11 als Ausgangsmaterialien eingesetzt. Die Reaktionsfähigkeit von 2 gegenüber Methyljodid und Acylierungsmitteln wird beschrieben.
    Type of Medium: Electronic Resource
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  • 3
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 105 (1972), S. 805-812 
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Amidoximes, I Synthesis and Acylation Reactions of a Semicyclic Amidoxime, 2-Oximino-1.2.3.4-tetrahydroquinoxalineAddition of hydroxylamine to N-(cyanomethyl)-ophenylenediamine (1) followed by cyclization with concomitant loss of NH3 gave 2-oximino-1.2.3.4-tetrahydroquinoxaline as the amidooxime tautomer 4 a. Various types of acylderivatives (5, 6, 9, 11 and 12) were prepared. 11 and its N5-acyl derivatives are the first examples of the [1.2.4]oxadiazolo[4.3-a]quinoxaline system.
    Notes: Addition von Hydroxylamin an N-Cyanmethyl-o-phenylendiamin (1) und nachfolgende Cyclisierung unter Ammoniakaustritt ergab 2-Oximino-1.2.3.4-tetrahydro-chinoxalin in Form des Amido-oxim-Tautomeren 4a. Es wurden verschiedene Typen von Acylderivaten (5, 6, 9, 11 und 12) hergestellt. 11 und seine N5-Acylderivate (12) sind die ersten Vertreter des [1.2.4]Oxadiazolo[4.3-a]chinoxalin-Ringsystems.
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
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  • 4
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 103 (1970), S. 3605-3614 
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Reaction of Cotarnone with Ammonia. Formation and Transformations of Cotarnimine, a Stable Atraldimine BaseDue to a competition of the vinyl and formyl group cotarnone (2) reacts with ammonia at temperatures below 20° to give a stable araldimine base 8, whereas at 80° norcotarnine (4) is formed by cyclisation. As supported by preparative and spectroscopic evidence, 4, is not formed by internal cyclisation of the imine 8, but presumably by addition of ammonia to the vinyl group of 2 and subsequent condensation.
    Notes: Bedingt durch eine Konkurrenz der Vinyl- und Formylgruppe entsteht bei der Reaktion des Cotarnons (2) mit Ammoniak unter 20° eine stabile kristalline Araldimin-Base 8, bie 80° dagegen durch Cyclisierung Norcotarnin (4). Aufgrund präparativer und spektroskopischer Untersuchungen wird angenommen, daß 4 nicht durch eine innermolekulare Cyclisierung des Imins 8, sondern durch Ammoniakaddition an die Vinylgruppe von 2 und nachfolgende Kondensation entsteht.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
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  • 5
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 105 (1972), S. 813-819 
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Amidoximes, II Redox Aromatization of 2-Oximino-1.2.3.4-tetrahydroquinoxaline and Its Acyl Derivatives2-Oximino-1.2.3.4-tetrahydroquinoxaline (1) in boiling acetic anhydride yielded 2-acetaminoquinoxaline (6). This unusual aromatization proceeds via the N4.O-diacetyl derivative 2a by synchronous elimination of the N4-acetyl and acetoxy groups as acetic anhydride. With palladium charcoal in solution both 1 and 3 gave 2-aminoquinoxaline (7). 7 was also obtained in quantitative yield by thermolysis of 3. The latter reaction parallels the transformation of N4-substituted 1.2.4-oxadiazolin-5-ones via azomethine nitrenes into amidines and is the first example of this process with condensed 1.2.4-oxadiazoles.
    Notes: Aus 2-Oximino-1.2.3.4-tetrahydro-chinoxalin (1) entsteht in siedendem Acetanhydrid 2-Acetamino-chinoxalin (6). Diese eigenartige Aromatisierung vollzieht sich aus dem N4. O-Diacetylderivat 2a als Zwischenstufe durch eine synchrone Abspaltung der N4-Acetyl- und der Oxim-Acetoxygruppe als Acetanhydrid. 1 und 3 liefern mit Palladiumkohle in Lösung 2-Amino-chinoxalin (7). 3 gibt rein thermolytisch fast quantitativ 7; der Prozeß ist der über Azomethin-nitrene führenden Umwandlung N4-substituierter 1.2.4-Oxadiazolone-(5) in Amidine analog und wurde jetzt erstmals an kondensierten 1.2.4-Oxadiazolen beobachtet.
    Type of Medium: Electronic Resource
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  • 6
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 107 (1974), S. 2563-2568 
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Amidoximes, IV. Dehydrogenation of a β-Hydroxylamino Amidoxime with azodicarboxylic Ester3-Hydroxylamino-2,3-diphenylpropionamide oxime (6), obtained from 2,3-diphenylacrylonitrile (5) by double addition of hydroxylamine, gave with the azodicarboxylate 2 via the β-nitroso-(isonitroso-)amide oxime 13a/13b 5-amono-3,4-diphenylisoxazole (7). From 13b 7 is formed by selective cyclisation (to 16) followed by selective elimination of hydroxylamine. Neither the structural isomer 3-aminoisoxazole 8 nor the 5-hydroxylamino derivative 15 were formed in this process.
    Notes: Das aus 2,3-Diphenylcrylonitril (5) durch doppelte Hydroxylamin-Addition erhaltene 3-Hydroxylamino-2,3-diphenylpropionamid-oxim (6) bildet mit dem Azodicarbonester 2 über das β-Nitroso-(isonitroso-)amidoxim 13a/13b 5-amino-3,4-diphenylisoxazol (7). 7-entsteht aus 13b durch selektive Cyclisierung (zu 16) und nachfolgende selektive Hydroxylamin-Eliminierung, Dieser Prozeß ergab weder das strukturisomere 3-Aminoisoxazol 8 noch das 5-Hydroxylamino-Derivat 15.
    Type of Medium: Electronic Resource
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  • 7
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 107 (1974), S. 2794-2795 
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Type of Medium: Electronic Resource
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  • 8
    ISSN: 0075-4617
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Chemistry of Heterocyclic Pseudobasic Aminoalcohols, XXXVII1).  -  A New Type of Isoquinoline Ring Formation by DisproportionationOn heating with primary aliphatic amines in aqueous alcohol cotarnone (1) undergoes ring closure combined with a redox disproportionation to give the tetrahydroisoquinoline 10 and the terrahydroisoquinolone 11. The compounds 10 and 11 are not formed by a transformation of the pseudobase 9.
    Notes: Beim Erwärmen mit aliphatischen primären Aminen in wäßrigem Alkohol ergibt Cotarnon (1) in einer Ringschlußreaktion unter Redox-Disproportionierung das Tetrahydrioisochinolin 10 und das Tetrahydroisochinolon 11 Die Möglichkeit der Entstehung von 10 und 11 durch Umwandlung der Pseudobase 9 wurde ausgeschlossen.
    Type of Medium: Electronic Resource
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  • 9
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Cotarnonoxim (4) ergibt in Äthanol mit Kaliumcyanid vorzugsweise das Nitril 9, mit Kalilauge das Dihydroisocarbostyril 5. Kalilauge und eine katalytische Kaliumcyanidmenge liefern den Isochinolin-Abkömmling 10.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
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  • 10
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 99 (1966), S. 273-280 
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Die Hydrazonderivate 2e-h des Cotarnons (1) werden durch katalytische Kaliumcyanid-Mengen in alkalischem Alkohol in das Isochinolinderivat 4 umgewandelt. Cotarn-azin (5) ergibt unter ähnlichen Bedingungen ein Gemisch von 4 und 6, ohne Cyanidkatalysator das Derivat 7 des Biisochinolyls-(2.2′).
    Type of Medium: Electronic Resource
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