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

Research output: Contribution to journalArticle

11 Citations (Scopus)

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.

LanguageEnglish
Pages1340-1345
Number of pages6
JournalBeilstein Journal of Organic Chemistry
Volume9
DOIs
Publication statusPublished - 5 Jul 2013

Fingerprint

Lactams
Azides
Cyclization
Carbon Monoxide
benzofuran
oxindole
indoline
azobis(isobutyronitrile)

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

Cite this

Ueda, Mitsuhiro ; Uenoyama, Yoshitaka ; Terasoma, Nozomi ; Doi, Shoko ; Kobayashi, Shoji ; Ryu, Ilhyong ; Murphy, John A. / A construction of 4,4-spirocyclic γ-lactams by tandem radical cyclization with carbon monoxide. In: Beilstein Journal of Organic Chemistry . 2013 ; Vol. 9. pp. 1340-1345.
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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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A construction of 4,4-spirocyclic γ-lactams by tandem radical cyclization with carbon monoxide. / Ueda, Mitsuhiro; Uenoyama, Yoshitaka; Terasoma, Nozomi; Doi, Shoko; Kobayashi, Shoji; Ryu, Ilhyong; Murphy, John A.

In: Beilstein Journal of Organic Chemistry , Vol. 9, 05.07.2013, p. 1340-1345.

Research output: Contribution to journalArticle

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