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

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11 Citations (Scopus)
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Abstract

A straightforward synthesis of 4,4-spirocyclic indol gamma-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 degrees C gave the desired 4,4-spirocyclic indoline, benzofuran, and oxindole gamma-lactams in moderate to good yields.

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

Keywords

  • azaenynes
  • nitrogen
  • cycloaddition
  • heterocycles
  • acyl radicals
  • azidonation
  • tandem radical cyclization
  • carbon monoxide
  • oxindole alkaloids
  • centered radicals
  • iodoaryl allyl azides
  • carbonylations
  • azides
  • free radical
  • 4,4-spirocyclic indol gamma-lactams

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