An efficient three-step synthesis of cyclopenta[b]pyrans via 2-donor-substituted fischer ethenylcarbenechromium complexes

Armin De Meijere, Heiko Schirmer, Frank Stein, Frank Funke, Michael Duetsch, Yao Ting Wu, Mathias Noltemeyer, Thomas Belgardt, Burkhard Knieriem

研究成果: Article

13 引文 斯高帕斯(Scopus)

摘要

A wide range of cyclopenta[b]pyrans 4 has been synthesized in a one-pot reaction by treatment of different 2-donorsubstituted ethenylcarbenechromium complexes 2 with alkynes in THF in moderate to excellent yields (41-90% for 14 out of 25 examples). The starting materials 2 are readily available in good to excellent yields (76-99% for 25 out of 36 examples) by Michael addition of amines, alcohols and thiols, respectively, to the corresponding alkynylcarbenechromium complexes 1. Due to their 10 π-electrons in a cross-conjugated bicyclic system, cyclopenta[b]pyrans have been termed pseudoazulenes, as they indeed have similar UV/Vis-spectroscopic properties.

原文English
頁(從 - 到)4132-4148
頁數17
期刊Chemistry - A European Journal
11
發行號14
DOIs
出版狀態Published - 2005 七月 4

    指紋

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Organic Chemistry

引用此

De Meijere, A., Schirmer, H., Stein, F., Funke, F., Duetsch, M., Wu, Y. T., Noltemeyer, M., Belgardt, T., & Knieriem, B. (2005). An efficient three-step synthesis of cyclopenta[b]pyrans via 2-donor-substituted fischer ethenylcarbenechromium complexes. Chemistry - A European Journal, 11(14), 4132-4148. https://doi.org/10.1002/chem.200500043