4.7 Article

Bioinspired cyclization of in situ generated γ-indolyl β,γ-unsaturated α-keto esters via an oxidative enamine process: facile approaches to pyrano[2,3-b]indoles

Journal

ORGANIC CHEMISTRY FRONTIERS
Volume 8, Issue 22, Pages 6337-6343

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/d1qo00996f

Keywords

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Funding

  1. Taishan Scholars Construction Projects of Shandong [tsqn201812075]
  2. Natural Science Foundation of Shandong Province for Distinguished Yong Scholars [ZR2020JQ07]
  3. Youth Innovation Science and Technology Plan of Colleges and Universities in Shandong Province [2019KJC003]
  4. Natural Science Foundation of China [21702115]
  5. Natural Science Foundation of Shandong Province, China [ZR2017BB028, ZR2019PB020, ZR2019MB010]
  6. Qingdao University of Science Technology

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A bioinspired cyclization reaction was developed using in situ generated substrates and an oxoammonium salt, leading to the synthesis of pyrano[2,3-b]indoles, which are bioactive compounds, in good yields up to 86% under mild conditions.
A bioinspired cyclization of in situ generated gamma-indolyl beta,gamma-unsaturated alpha-ketoesters with an oxoammonium salt via an oxidative enamine process has been developed. Under mild conditions, the reactions afforded pyrano[2,3-b]indoles, which are found in a wide range of bioactive compounds, in good yields (up to 86% yield).

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