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Reactions of 1,5-π-cyclization of gem-difluoro-substituted azomethine ylides involving an aromatic ring

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Abstract

Reactions of N-(5-R-furan-2-ylmethylidene)anilines with difluorocarbene proceeds through intermediate azomethine ylides suffering 1,5-π-cyclization to yield 6,6-difluorocyclopropa[b]furo[2,3-c]pyrrole and/or 4,4,6,6-tetrafluorocyclopropa[b]furo[2,3-c]pyrrole. The heating of these compounds without solvent resulted in high yields of 2,5-disubstituted 7-fluoro-4,5-dihydrofuro[3,2-c]pyridin-4(5H)-ones.

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Authors and Affiliations

  1. St. Petersburg State University, St. Petersburg, 198504, Russia

    I. V. Voznyi, M. S. Novikov, A. F. Khlebnikov & R. R. Kostikov

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  1. I. V. Voznyi
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  2. M. S. Novikov
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  3. A. F. Khlebnikov
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  4. R. R. Kostikov
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Original Russian Text © I.V. Voznyi, M.S. Novikov, A.F. Khlebnikov, R.R. Kostikov, 2006, published in Zhurnal Organicheskoi Khimii, 2006, Vol. 42, No. 5, pp. 708–714.

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Voznyi, I.V., Novikov, M.S., Khlebnikov, A.F. et al. Reactions of 1,5-π-cyclization of gem-difluoro-substituted azomethine ylides involving an aromatic ring. Russ J Org Chem 42, 689–695 (2006). https://doi.org/10.1134/S1070428006050071

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  • DOI: https://doi.org/10.1134/S1070428006050071

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