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  • Carbothioic acid anilides  (1)
  • Cycloalkeno[c]pyridines  (1)
  • Enamino ketones  (1)
  • Pyrans  (1)
  • 1
    ISSN: 1434-4475
    Keywords: Cycloalkeno[c]pyridines ; Cycloalkeno[c]thiopyrans ; Reactions with malononitrile
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Zusammenfassung Es wird ein neuer Zugang zu Cycloalkeno[c]pyridinen (2) und Cycloalkeno[c]thiopyranen (5) mittels Reaktion von Malononitril mit Enaminen cyclischer β-Ketocarbothionsäureaniliden aufgezeigt. Die Strukturaufklärung der erhaltenen Verbindungen basiert auf massenspektroskopischen Daten. Die Reaktion wird als Folge von Addition, Eliminierung und Cyclisierung diskutiert.
    Notes: Abstract A new route to the cycloalkeno-pyridines2 and cycloalkeno-thiopyrans5 by the reaction of malononitrile with enamines of cyclic β-ketocarbothionic acid anilides is presented. The elucidation of the structure of compounds obtained is based on MS spectral data. The reaction is proposed to be a sequence of addition, elimination and cyclization.
    Type of Medium: Electronic Resource
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  • 2
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1989 (1989), S. 1131-1134 
    ISSN: 0170-2041
    Keywords: Dienamines, cyclic ; Carbothioic acid anilides ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Morpholino enamines 1,2, and 3 of 2-(cyclopentylidene)-1-cyclopentanone, 2-(1-cyclohexenyl)-1-cyclohexanone, and 2-(cycloheptylidene)-1-cycloheptanone, respectively, react with aryl isothiocyanates to yield 1-cycloalkene-1-carbothioic acid anilides 4, 5, and 6, respectively. Compounds 4 and 5 react with malononitrile to give the hexahydroisoquinolines 9 and the cyclopenta[c]pyridine 11, respectively.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
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  • 3
    ISSN: 0170-2041
    Keywords: Amino sugars ; Carbohydrates ; Enamino ketones ; Hetero-Diels-Alder reactions ; Pyrans ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The hetero-Diels-Alder reaction of the phenylthio-activated N-monoacyl- and N,N-diacyl-enamino ketones 8a-c containing a methyl group at position 2 of the oxadiene with the electron-rich dienophiles 9a-c yields the exo/endo adducts 10a-d and 11a-d in 82-95% yield with the endo adducts as the main products. The enamino ketone 8d with a S-ethyl group at C-3 does not react. Hydrogenation of 11a with Raney nickel in THF leads to the desulfurized dihydropyran 12, whereas in MeOH gives stereoselectively the perhydrophthalimido derivative 13, which, after deprotection, yields the β-methyl glycoside 14 of rac-4-deoxydaunosamine. Under similar conditions 10c is converted into the β-ethyl glycoside 15 of rac-N-benzoyl-4-deoxyristosamine. Stereoselective hydroboration of 12 affords 17 and subsequent cleavage of the protecting group leads to the β-methyl glycoside 18 of rac-acosamine.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
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