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Arylsulfonylureido- und Arylsulfonylamidoacyl-Derivate von Hydroxy- und Oxocycloalkanen als potentielle Antidiabetica, 1. Mitt.:cis-2-Tosylureido-cyclohexanol

Arylsulfonylureido- and arylsulfonyl-amidoacyl-derivatives of hydroxy- and oxocycloalkanes as potential antidiabetic drugs. I.

  • Organische Chemie und Biochemie
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Abstract

The preparation of 2-tosylamino-cis-hexahydro-3H-benzo[d] oxazoline either from trans-2-iodocyclohexyl isocyanate and tosylamide-Na or fromcis-2-aminocyclohexanol and methyl tosyliminodithiocarbonate is described. Alkaline hydrolysis of this compound yieldscis-2-tosylureidocyclohexanol, which can also be obtained by direct reaction ofcis-2-aminocyclohexanol with tosylethylurethane or tosyl isocyanate, or by reactingcis-2-carbethoxyaminocyclohexanol with tosylamide-Na.

Zusammenfassung

Es wird die Darstellung von 2-Tosylamino-cis-hexahydro-3H-benzo[d]oxazolin austrans-2-Jodcyclohexylisocyanat und Tosylamid-Na bzw.cis-2-Aminocyclohexanol und Tosyliminodithiokohlensäuremethylester beschrieben. Die alkal. Hydrolyse dieser Verbindung führt zucis-2-Tosylureido-cyclohexanol, welches auch durch direkte Umsetzung voncis-2-Aminocyclohexanol mit Tosyläthylurethan oder Tosylisocyanat bzw. durch Umsatz voncis-2-Carbäthoxyamino-cyclohexanol mit Tosylamid-Na erhalten werden kann.

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Authors and Affiliations

  1. Institut für organische und pharmazeutische Chemie der Universität Innsbruck, Innsbruck, Österreich

    H. Bretschneider & H. Egg

Authors
  1. H. Bretschneider
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  2. H. Egg
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Bretschneider, H., Egg, H. Arylsulfonylureido- und Arylsulfonylamidoacyl-Derivate von Hydroxy- und Oxocycloalkanen als potentielle Antidiabetica, 1. Mitt.:cis-2-Tosylureido-cyclohexanol. Monatshefte für Chemie 103, 1377–1384 (1972). https://doi.org/10.1007/BF00904520

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  • DOI: https://doi.org/10.1007/BF00904520

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