Intramolecular cycloaddition of N-phthalimidoaziridines to double and triple carbon–carbon bonds
2009; Elsevier BV; Volume: 50; Issue: 44 Linguagem: Inglês
10.1016/j.tetlet.2009.08.015
ISSN1873-3581
AutoresAlena S. Pankova, Vladimir V. Voronin, Михаил А. Кузнецов,
Tópico(s)Synthesis and Reactions of Organic Compounds
ResumoThermolysis of 3-(2-allyloxyphenyl)- or 3-(2-propargyloxyphenyl)-1-phthalimidoaziridine-2-carboxylic acid derivatives results in stereospecific intramolecular cycloaddition of intermediate N-phthalimidoazomethine ylides to double or triple carbon–carbon bonds. This leads to condensed N-phthalimidopyrrolidines, N-phthalimidopyrrolines, or products of their subsequent transformations. On the other hand, thermolysis of similar dimethyl 3-aryl-1-phthalimidoaziridine-2,2-dicarboxylates gives exclusively 5-methoxyoxazoles, the products of a competitive 1,5-dipolar electrocyclization.
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