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Molbank 2018, 2018(2), M992; https://doi.org/10.3390/M992

1-Adamantylamidoxime

1
Laboratorio de Síntesis de Heterociclos Bioactivos, Departamento de Farmacia, Facultad de Química, Pontificia Universidad Católica de Chile, Casilla 306, Avda. Vicuña Mackenna 4860, Macul, 7820436 Santiago, Chile
2
Facultad de Medicina y Ciencia, Universidad San Sebastián, Lota 2465, Providencia, 7510157 Santiago, Chile
*
Author to whom correspondence should be addressed.
Received: 6 April 2018 / Revised: 13 April 2018 / Accepted: 17 April 2018 / Published: 19 April 2018
(This article belongs to the Special Issue Molecules from Catalytic Processes)
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Abstract

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. View Full-Text
Keywords: catalysis; Lewis acid; aliphatic amidoximes; adamantane; 11β-HSD1; 1,2,4-oxadiazole catalysis; Lewis acid; aliphatic amidoximes; adamantane; 11β-HSD1; 1,2,4-oxadiazole
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Diethelm, B.; Lagos, C.F.; Recabarren-Gajardo, G. 1-Adamantylamidoxime. Molbank 2018, 2018, M992.

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