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Molecules 2005, 10(3), 521-533; doi:10.3390/10030521
Article

Investigations on the Formation of 4-Aminobicyclo[2.2.2]-octanones

1,* , 1, 2, 3, 1 and 1
1 Institute of Pharmaceutical Sciences, Pharmaceutical Chemistry, Karl-Franzens-University, Universitätsplatz 1, A-8010 Graz, Austria 2 Institute of Chemistry, Karl-Franzens-University, Universitätsplatz 1, A-8010 Graz, Austria 3 Institute of Chemical Technology of Organic Materials, Erzherzog-Johann University, Stremayrgasse 26/1, A-8010 Graz, Austria
* Author to whom correspondence should be addressed.
Received: 13 September 2004 / Revised: 10 January 2005 / Accepted: 10 January 2005 / Published: 13 May 2005
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Abstract

Benzylidene acetone reacts with thiocyanates derived from secondary amines in a one-pot reaction to give 4-aminobicyclo[2.2.2]octan-2-ones. The reaction mixture was investigated for the presence of possible intermediates using GC-MS. These intermediates – diketones and enamines – were prepared and exposed to the same reaction conditions to examine the reaction mechanism. The reaction of ethyl styryl ketone with thiocyanates of secondary amines yielded cyclohexanone derivatives instead of the expected bicyclo- octanones. Their structures were established by means of a single crystal structure analysis.
Keywords: α; β-Unsaturated ketones; cyclization; dialkylammonium thiocyanates; aminobicyclo[2.2.2]octanones; enamines α; β-Unsaturated ketones; cyclization; dialkylammonium thiocyanates; aminobicyclo[2.2.2]octanones; enamines
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.

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MDPI and ACS Style

Seebacher, W.; Kröpfl, D.; Belaj, F.; Saf, R.; Hüfner, A.; Weis, R. Investigations on the Formation of 4-Aminobicyclo[2.2.2]-octanones. Molecules 2005, 10, 521-533.

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