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Intra- and intermolecular thermal transformations of 2-acyl- and 2-alkoxycarbonyl-N-phthalimidoaziridines

  • M. A. KuznetsovEmail author
  • V. V. Voronin
Article

Heating 2-acyl- and 2-alkoxycarbonyl-N-phthalimidoaziridines leads to substituted oxazoles in 45-65% yield. Only esters of oxazolecarboxylic acids are formed when the aziridine contains acyl and alkoxy groups. The thermolysis of the same aziridines in the presence of N-phenylmaleimide and the dimethyl ester of acetylenedicarboxylic acid gives both oxazoles and the products of 1,3-dipolar cycloaddition from aziridines with two substituents at the carbon atoms but only oxazoles from trisubstituted aziridines.

Keywords

N-aminopyrrolidines N-aminopyrrolines aziridines azomethinylids 1,3-oxazoles pyrroles 1,3-dipolar cycloaddition 

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Copyright information

© Springer Science+Business Media, Inc. 2011

Authors and Affiliations

  1. 1.St. Petersburg State UniversitySt. PetersburgRussia

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