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

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

Pure And Applied Chemistry

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13 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 language	English
Pages (from-to)	1340-1345
Number of pages	6
Journal	Beilstein Journal of Organic Chemistry
Volume	9
DOIs	https://doi.org/10.3762/bjoc.9.151
Publication status	Published - 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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10.3762/bjoc.9.151

Construction of 4 4 spirocyclicFinal published version, 389 KB

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

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.",

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",

author = "Mitsuhiro Ueda and Yoshitaka Uenoyama and Nozomi Terasoma and Shoko Doi and Shoji Kobayashi and Ilhyong Ryu and Murphy, {John A.}",

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doi = "10.3762/bjoc.9.151",

language = "English",

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T1 - A construction of 4,4-spirocyclic γ-lactams by tandem radical cyclization with carbon monoxide

AU - Ueda, Mitsuhiro

AU - Uenoyama, Yoshitaka

AU - Terasoma, Nozomi

AU - Doi, Shoko

AU - Kobayashi, Shoji

AU - Ryu, Ilhyong

AU - Murphy, John A.

PY - 2013/7/5

Y1 - 2013/7/5

N2 - 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.

AB - 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.

KW - azaenynes

KW - nitrogen

KW - cycloaddition

KW - heterocycles

KW - acyl radicals

KW - azidonation

KW - tandem radical cyclization

KW - carbon monoxide

KW - oxindole alkaloids

KW - centered radicals

KW - iodoaryl allyl azides

KW - carbonylations

KW - azides

KW - free radical

KW - 4,4-spirocyclic indol gamma-lactams

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U2 - 10.3762/bjoc.9.151

DO - 10.3762/bjoc.9.151

M3 - Article

VL - 9

SP - 1340

EP - 1345

JO - Beilstein Journal of Organic Chemistry

JF - Beilstein Journal of Organic Chemistry

SN - 1860-5397

ER -

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

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Keywords

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