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

Ueda, Mitsuhiro and Uenoyama, Yoshitaka and Terasoma, Nozomi and Doi, Shoko and Kobayashi, Shoji and Ryu, Ilhyong and Murphy, John A. (2013) A construction of 4,4-spirocyclic γ-lactams by tandem radical cyclization with carbon monoxide. Beilstein Journal of Organic Chemistry, 9. pp. 1340-1345. ISSN 1860-5397

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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.