Catalytic Synthesis of Dibenzazepines and Dibenzazocines by 7-Exo- and 8-Endo-Dig-Selective Cycloisomerization

Mamoru Ito*, Asahi Takaki, Moeka Okamura, Kyalo Stephen Kanyiva, Takanori Shibata

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

Abstract

The 7-exo- and 8-endo-dig-selective gold-catalyzed cycloisomerizations of 2-propargylamino biphenyl derivatives were developed. The reaction of terminal alkynes gave dibenzo[b,d]azepines by 7-exo-dig cycloisomerization. In contrast, when internal alkynes were subjected to the reaction, 8-endo-dig cycloisomerization proceeded to provide dibenzo[b,d]azocines. The nucleophilicity at the reaction site and the electron-withdrawing effect of a tosyl group were important for the present selective transformation. This protocol could be used for ynamide substrates and a silver-catalyzed reaction gave 7-exo-dig products selectively.

Original languageEnglish
Pages (from-to)1688-1692
Number of pages5
JournalEuropean Journal of Organic Chemistry
Volume2021
Issue number11
DOIs
Publication statusPublished - 2021 Mar 19

Keywords

  • 7-Exo-dig
  • 8-Endo-dig
  • Cycloisomerization
  • Gold catalysis
  • NHC ligands

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

Fingerprint

Dive into the research topics of 'Catalytic Synthesis of Dibenzazepines and Dibenzazocines by 7-Exo- and 8-Endo-Dig-Selective Cycloisomerization'. Together they form a unique fingerprint.

Cite this