Gold-Catalyzed Cascade and Divergent Synthesis of Indolobenzazepines and Indoloquinolines from Nitrogen-Tethered 1,8-Diynes

Mamoru Ito*, Hideaki Onoda, Asahi Takaki, Takanori Shibata*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

3 Citations (Scopus)

Abstract

We describe the divergent construction of two nitrogen-containing polycyclic systems by gold-catalyzed cycloisomerizations. The gold-catalyzed cascade hydroamination and 7-endo-dig-selective cycloisomerization of nitrogen-tethered 1,8-diynes yielded indolo[1,7-ab]benzazepines in one pot. In contrast, when Johnphos-coordinated gold catalyst was used, the same 1,8-diynes were transformed into indolo[1,2-a]quinolines by 6-endo-dig-selective cycloisomerization along with rearrangement of the substituent on one of the alkynes. The reaction of a naphthalene-tethered substrate provided a helically chiral aza[6]helicene.

Original languageEnglish
Article numbere202101337
JournalEuropean Journal of Organic Chemistry
Volume2022
Issue number15
DOIs
Publication statusPublished - 2022 Apr 21

Keywords

  • Alkynes
  • Cycloisomerization
  • Divergent synthesis
  • Gold
  • Silver

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

Fingerprint

Dive into the research topics of 'Gold-Catalyzed Cascade and Divergent Synthesis of Indolobenzazepines and Indoloquinolines from Nitrogen-Tethered 1,8-Diynes'. Together they form a unique fingerprint.

Cite this