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

doi:10.3762/bjoc.9.151

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

Beilstein J Org Chem. 2013 Jul 5:9:1340-5. doi: 10.3762/bjoc.9.151. eCollection 2013.

Authors

Mitsuhiro Ueda¹, Yoshitaka Uenoyama, Nozomi Terasoma, Shoko Doi, Shoji Kobayashi, Ilhyong Ryu, John A Murphy

Affiliation

¹ Department of Chemistry, Graduate School of Science, Osaka Prefecture University, Sakai, Osaka 599-8531, Japan.

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.

Keywords: 4,4-spirocyclic indol γ-lactams; carbon monoxide; free radical; iodoaryl allyl azides; tandem radical cyclization.