Ring opening of 2-(cyanomethyl)aziridines by acid chlorides: synthesis of novel 4-amino-2-butenenitrile derivatives through intermediate aziridinium salts |
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Authors: | Matthias D’hooghe |
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Institution: | Department of Organic Chemistry, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, B-9000 Ghent, Belgium |
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Abstract: | 1-Arylmethyl-2-(cyanomethyl)aziridines were transformed into novel N-arylmethyl-N-(2-chloro-3-cyanopropyl)amides as the major reaction products upon treatment with acid chlorides in CH2Cl2 through the ring opening of intermediate aziridinium salts. Subsequently, N-arylmethyl-N-(2-chloro-3-cyanopropyl)amides were converted into stable N-arylmethyl-N-(3-cyano-2-propenyl)amides for the first time by means of a dehydrochlorination mediated by Et3N in CH2Cl2. |
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Keywords: | 2-(Bromomethyl)aziridines Aziridinium salts Ring opening Regioselectivity Amino nitriles |
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