Reaction of functionalized azomethine ylides with acetylenic dipolarophiles: the facile synthesis of functionalized 2H- and 1H-pyrroles

  • Kawashima K
  • Hiromoto M
  • Hayashi K
 et al. 
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Abstract

The reaction of functionalized azomethine ylides as C-unsubstituted nitrile ylide equivalents with acetylenic dipolarophiles is mentioned. Therein, the initially formed cycloadducts, 2,5-dihydropyrroles, by the reaction of the azomethine ylides with substituted acetylenes, undergo a fission reaction to afford 2H-pyrroles and the parent heterocyclic system. Some 2H-pyrroles isomerized to 1H-pyrroles under both thermal and acidic conditions. © 2006.

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Authors

  • Keisuke Kawashima

  • Masanori Hiromoto

  • Kyohei Hayashi

  • Akikazu Kakehi

  • Motoo Shiro

  • Michihiko Noguchi

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