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Arylsulfonylureido- und Arylsulfonylamidoacyl-Derivate von Hydroxy- und Oxocycloalkanen als potentielle Antidiabetica, 4. Mitt.: 3-Arylsulfonylcarbamoyl-cis-hexahydro-3H-benzo[d]oxazol-2-one und deren Umwandlung incis-2-Arylsulfonylureidocyclohexanole

Arylsulfonylureido- and arylsulfonylamidoacyl-derivatives of hydroxy- and oxocycloalkanes as potential antidiabetic drugs. IV

  • Organische Chemie und Biochemie
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Monatshefte für Chemie / Chemical Monthly Aims and scope Submit manuscript

Abstract

trans-2-Chlorocyclohexylcarbamate is treated with arylsulfonylisocyanates to yield the corresponding arylsulfonylallophanates, which with NaH in DMSO cyclize to 3-arylsulfonylcarbamoyl-cis-hexahydro-3H-benzo[d]oxazolones. The latter are hydrolysed by aqueous alkali tocis-2-arylsulfonylureidocyclohexanols.

Zusammenfassung

trans-2-Chlorcyclohexylcarbamat wird mit Arylsulfonylisocyanaten zu den entsprechenden Arylsulfonylallophanaten umgesetzt, die sich mit NaH inDMSO zu den 3-Arylsulfonylcarbamoyl-cis-hexahydro-3H-benzo[d]oxazolonen cyclisieren. Letztere werden mit wäßr. Alkali zu dencis-2-Arylsulfonylureidocyclohexanolen hydrolysiert.

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Literatur

  1. H. Egg, 3. Mitt., Mh. Chem.103, 1391 (1972).

    Google Scholar 

  2. H. Bretschneider undH. Egg, 4. vorl. Mitt., Mh. Chem.100, 2131 (1969).

    Google Scholar 

  3. M. Mousseron, F. Winternitz undM. Mousseron-Canet, Bull. Soc. Chim. France1953, 737.

  4. C. Heathcock undA. Hassner, Angew. Chem.75, 344 (1965).

    Google Scholar 

  5. T. A. Foglia undD. Swern, J. org. Chem.31, 3625 (1966);32, 75 (1967).

    Google Scholar 

  6. J. I. Jones, J. Chem. Soc.1957, 2735.

  7. M. E. Dyen undD. Swern, Chem. Rev.67, 197 (1967).

    Google Scholar 

  8. M. M. Baizer, US-Pat. 3 168 525; Chem. Abstr.62, 16253 (1965).

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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, 4. Mitt.: 3-Arylsulfonylcarbamoyl-cis-hexahydro-3H-benzo[d]oxazol-2-one und deren Umwandlung incis-2-Arylsulfonylureidocyclohexanole. Monatshefte für Chemie 103, 1394–1398 (1972). https://doi.org/10.1007/BF00904523

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  • DOI: https://doi.org/10.1007/BF00904523

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