EventsThe 12th International Electronic Conference on Synthetic Organic Chemistry
Event submissions
Published
with-doi10.3390/ecsoc-12-01230
This submission belongs to the session a. General Organic Synthesis of the event The 12th International Electronic Conference on Synthetic Organic Chemistry
Published date
06 Nov, 2008
Citation
Matthias D’hooghe, Norbert De Kimpe, Highly Regioselective Synthesis of Functionalized Aminonitriles Starting from 2-(w-cyanoalkyl)aziridines, in Proceedings of The 12th International Electronic Conference on Synthetic Organic Chemistry, 1 November–30 November 2008, MDPI: Basel, Switzerland, doi: 10.3390/ecsoc-12-01230
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Highly Regioselective Synthesis of Functionalized Aminonitriles Starting from 2-(w-cyanoalkyl)aziridines

Matthias D’hooghe 1
Norbert De Kimpe 1
1. Department of Organic Chemistry, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, B-9000 Ghent, Belgium
Abstract
1-arylmethyl-2-(bromomethyl)aziridines were transformed into the corresponding 2-(cyanomethyl)aziridines and 2-(2-cyanoethyl)aziridines upon treatment with potassium cyanide in DMSO and a-lithiated trimethylsilylacetonitrile in THF, respectively. Further elaboration of 1-arylmethyl-2-(cyanomethyl)aziridines afforded 4-amino-2-butenenitriles, 3,4-diaminobutanenitriles and 2-aminocyclopropanecarbonitriles. Additionally, 1-arylmethyl-2-(2-cyanoethyl)aziridines were efficiently converted into biologically relevant 2-(aminomethyl)-cyclopropanecarbonitriles.
Keywords
n/a
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