4.7 Article

Iron(iii)-catalyzed tandem annulation of indolyl-substituted p-quinone methides with ynamides for the synthesis of cyclopenta[b]indoles

Journal

CHEMICAL COMMUNICATIONS
Volume 58, Issue 62, Pages 8710-8713

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/d2cc03252j

Keywords

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Funding

  1. NSFC [21825104, 22071091, 21801103]
  2. China Postdoctoral Science Foundation [2020M683603]
  3. FRFCU [lzujbky-20210119, lzujbky2021-pd02]
  4. PCSIRT [IRT_15R28]

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The unique reactivity of indolyl-substituted p-QMs as a new type of two-carbon synthon in a novel iron(iii)-catalyzed tandem annulation has been explored for the first time. The (2+2) annulation/retro-4 pi electrocyclization/imino-Nazarov cyclization cascade reaction is characterized by an unusual structural reconstruction of indolyl-substituted p-QMs, leading to the rapid assembly of synthetically important functionalized cyclopenta[b]indoles.
The unique reactivity of indolyl-substituted p-QMs as a new type of two-carbon synthon has been explored for the first time in a novel iron(iii)-catalyzed tandem annulation. This (2+2) annulation/retro-4 pi electrocyclization/imino-Nazarov cyclization cascade reaction is characterized by an unusual structural reconstruction of indolyl-substituted p-QMs, leading to an expeditious assembly of synthetically important functionalized cyclopenta[b]indoles.

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