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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 31, 2001 - Issue 17
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Original Articles

BASE INDUCED REACTION OF AN AZETIDIN-2-ONE: FORMATION OF A NOVEL [1,4]-DIAZEPINEDIONE

Dashyant Dhanak SmithKline Beecham Pharmaceuticals, 1250 South Collegeville Road, P.O. Box 5089, Collegeville, PA, 19426-0989, U.S.A.
,
Deirdre M. B. Hickey SmithKline Beecham Pharmaceuticals, 1250 South Collegeville Road, P.O. Box 5089, Collegeville, PA, 19426-0989, U.S.A.
,
Malcolm L. Meeson SmithKline Beecham Pharmaceuticals, 1250 South Collegeville Road, P.O. Box 5089, Collegeville, PA, 19426-0989, U.S.A.
,
Richard L. Elliott SmithKline Beecham Pharmaceuticals, 1250 South Collegeville Road, P.O. Box 5089, Collegeville, PA, 19426-0989, U.S.A.
,
Andrew D. Shore SmithKline Beecham Pharmaceuticals, 1250 South Collegeville Road, P.O. Box 5089, Collegeville, PA, 19426-0989, U.S.A.
&
R. Curtis Haltiwanger SmithKline Beecham Pharmaceuticals, 1250 South Collegeville Road, P.O. Box 5089, Collegeville, PA, 19426-0989, U.S.A.
Pages 2713-2718 | Received 21 Nov 2000, Published online: 09 Nov 2006
 
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Abstract

A mild, base mediated conversion of an azetidin-2-one to the [1,4]-diazapinedione system is reported and a putative mechanistic pathway is proposed.

ACKNOWLEDGMENTS

We thank Dr. Tony Shaw and Dr. Andrew Edwards for useful discussions during the preparation of this manuscript.

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