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Molbank, Vol. 2018, Article M992: 1-Adamantylamidoxime

Molbank, Vol. 2018, Article M992: 1-Adamantylamidoxime

Molbank doi: 10.3390/M992

Authors: Benjamín Diethelm Carlos Lagos Gonzalo Recabarren-Gajardo

The title compound was prepared by the nucleophilic addition of hydroxylamine over 1-cyanoadamantane. The poor reactivity of the nitrile substrate, due to its scarcely electrophilic nature, prompted the need to employ several activating conditions. Energy supply via conventional heating, ultrasound, and microwave irradiation did not lead to product formation. Therefore, Lewis acid catalysis was attempted. Initial tests with ZnCl2 led to product formation in poor yields. Conversely, the use of AlCl3 led to the formation of the desired amidoxime in the moderate yield, which was further increased to an excellent yield by performing the reaction in a more concentrated medium. The structural identity of the title compound was proven by spectroscopic methods (IR, NMR). This compound was later employed as a starting material for the synthesis of 3,5-disubstituted 1,2,4-oxadiazole derivatives as potential 11β-HSD1 inhibitors.

Authors:   Diethelm, Benjamín ; Lagos, Carlos F.; Recabarren-Gajardo, Gonzalo
Journal:   Molbank
Volume:   2018
edition:   2
Year:   2018
Pages:   M992
DOI:   10.3390/M992
Publication date:   19-Apr-2018
Facts, background information, dossiers
  • reactivity
  • Nucleophilic addition
  • lead
  • inhibitors
  • Energy
  • acid catalysis
More about Molecular Diversity Preservation International
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