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  • 1
    Electronic Resource
    Electronic Resource
    Studies on 5-aminopyrazole derivatives synthesis of some new fused pyrazole derivatives (1984)
    Springer
    Monatshefte für Chemie 115 (1984), S. 431-436 
    Details
    ISSN: 1434-4475
    Keywords: Enaminonitriles ; Fused Pyrazoles
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Zusammenfassung Die Reaktion von 5-Amino-4-cyano-3-phenylpyrazol (1) mit Acrylnitril oder Ethylacrylate ergibt 4-Cyano-3-phenyl-4,5,6,7-tetrahydro-5-oxopyrazolo-[1,5-a]-pyrimidin (2). Die Reaktion von1 mit Harnstoff, Thioharnstoff und7. Ethyl acetoacetat ergibt die Pyrazolopyrimidinderivate6a,6b und7. Andererseits entsteht das Thioharnstoffderivat4 durch die Reaktion von1 mit Benzoylisothiocyanat. Diazotiertes1 koppelt mit Malononitril und Ethylcyanoacetat zu den Pyrazolopyrimidinen10 und11, die Kopplung mit α-chloroacetoacetic ester und Acetylaceton ergibt jedoch die Hydrazone12 und13.
    Notes: Abstract 5-Amino-4-cyano-3-phenylpyrazole (1) reacts with acrylonitrile or ethyl acrylate to yield 4-cyano-3-phenyl-4,5,6,7-tetrahydro-5-oxopyrazolo-[1,5-a]-pyrimidine (2). With urea, thiourea and ethyl acetoacetate1 gives the pyrazolopyrimidine derivatives6a,6b, and7 respectively. On the other hand, compound1 reacted with benzoylisothiocyanate to give the corresponding thiourea derivative4. Diazotized1 was coupled with malononitrile and ethyl cyanoacetate to yield the pyrazolopyrimidine derivatives10 and11, respectively, whereas on coupling with α-chloro acetoacetic ester and with acetylacetone the hydrazones12 and13 were obtained.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00810004
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  • 2
    Electronic Resource
    Electronic Resource
    A facile synthesis of substituted perhydro-1,3-thiazin-4-ones and 2-thioxoperhydro-4-pyrimidinones (1988)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1988 (1988), S. 983-987 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Eine einfache Synthese von substituierten Perhydro-1,3-thiazin-4-onen und 2-Thioxoperhydro-4-pyrimidinonenDie basisch katalysierte Cyclisierung der N-Propenoylthioharnstoffe 3 liefert je nach den Reaktionsbedingungen entweder 2,6-disubstituierte 2,3,5,6-Tetrahydro-4H-1,3-thiazin-4-one 4 oder 1,6-disubstituierte 2-Thiouracile 5. Unter denselben Reaktionsbedingungen können die Verbindungen 5 durch eine Art Dimroth-Umlagerung aus den 1,3-Thiazin-4-onen 4 erhalten werden.
    Notes: Depending on the reaction conditions either 2,6-disubstituted 2,3,5,6-tetrahydro-4H-1,3-thiazin-4-ones 4 or 1,6-disubstituted 2-thiouracils 5 are readily prepared by base-catalyzed cyclization of N-propenoylthioureas 3. Compounds 5 could also be obtained by Dimroth-type rearrangement of 1,3-thiazin-4-ones 4 under the same reaction conditions.
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198819881009
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  • 3
    Electronic Resource
    Electronic Resource
    Synthesis of polyfunctionally substituted pyridazines (1990)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1990 (1990), S. 293-296 
    Details
    ISSN: 0170-2041
    Keywords: Pyridazine, derivatives ; Pyrazolo-pyridazine, derivative ; Pyrido-pyridazine, derivative ; Isoxazolo-pyridazine, derivative ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The pyridazines 3, 4, 5, and 7 were obtained by reaction of the hydrazone derivatives 2 with several reagents. By treatment of 5 with acetic acid/hydrochloric acid, the pyrazolo[4,3-c]-pyridazine 6 was formed. The pyrido-pyridazine derivatives 8 and 9 were obtained by reaction of 2 and 3 with malononitrile and ethyl cyanoacetate, respectively, and the isoxazolo-pyridazines 11 by reaction of 3a, b with hydroxylamine hydrochloride in ethanolic sodium ethoxide solution. The intermediate 9 was separated by reaction of 3a, b with hydroxylamine hydrochloride in ethanolic sodium acetate solution.
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199019900153
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