A construction of 4,4-spirocyclic γ-lactams by tandem radical cyclization with carbon monoxide

Mitsuhiro Ueda, Yoshitaka Uenoyama, Nozomi Terasoma, Shoko Doi, Shoji Kobayashi, Ilhyong Ryu*, John A. Murphy

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

13 Scopus citations

Abstract

A straightforward synthesis of 4,4-spirocyclic indol γ-lactams by tandem radical cyclization of iodoaryl allyl azides with CO was achieved. The reaction of iodoaryl allyl azides, TTMSS and AIBN under CO pressure (80 atm) in THF at 80 °C gave the desired 4,4-spirocyclic indoline, benzofuran, and oxindole γ-lactams in moderate to good yields.

Original languageEnglish
Pages (from-to)1340-1345
Number of pages6
JournalBeilstein Journal of Organic Chemistry
Volume9
DOIs
StatePublished - 5 Jul 2013

Keywords

  • 4,4-spirocyclic indol γ-lactams
  • Carbon monoxide
  • Free radical
  • Iodoaryl allyl azides
  • Tandem radical cyclization

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