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Synthesis of 3- and 5-amino-5-(3)-(pyrrol-2-yl)isoxazoles |
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| Authors: | Lyubov' N Sobenina Vladislav N Drichkov Al'bina I Mikhaleva Olga V Petrova Igor A Ushakov Boris A Trofimov |
| Institution: | A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky Str., Irkutsk 664033, Russian Federation |
| Abstract: | 5-Amino-3-(pyrrol-2-yl)isoxazoles were selectively prepared by the reaction of 2-(2,2-dicyano-1-ethylthioethenyl)pyrroles with hydroxylamine in methanol. Under analogous conditions, 2-(2-carbamoyl-2-cyano-1-ethylthioethenyl) pyrroles with hydroxylamine gave 5-aminoisoxazoles and their structural isomers, 3-aminoisoxazoles (3-5% yield). The latter were selectively prepared by reacting 2-(2-carbamoyl-2-cyano-1-ethylthioethenyl)pyrroles with hydroxylamine in the presence of aqueous NaOH and from the products of intramolecular cyclization of 2-(2-carbamoyl-2-cyano-1-ethylthioethenyl)pyrroles, 1-ethylthio-3-iminopyrrolizines and hydroxylamine. |
| Keywords: | 5-Aminopyrrolylisoxazoles 3-Aminopyrrolylisoxazoles 2-(2-Cyano-1-ethylthioethenyl)pyrroles 1-Ethylthio-3-iminopyrrolizines Hydroxylamine |
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