Volume 32, Issue 51
Preparative Organic Chemistry
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ChemInform Abstract: Base Induced Reaction of an Azetidin-2-one: Formation of a Novel [1,4]-Diazepinedione.

Dashyant Dhanak

Dashyant Dhanak

SmithKline Beecham Pharm., Collegeville, PA 19426, USA

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Deirdre M. B. Hickey

Deirdre M. B. Hickey

SmithKline Beecham Pharm., Collegeville, PA 19426, USA

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Malcolm L. Meeson

Malcolm L. Meeson

SmithKline Beecham Pharm., Collegeville, PA 19426, USA

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Richard L. Elliott

Richard L. Elliott

SmithKline Beecham Pharm., Collegeville, PA 19426, USA

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Andrew D. Shore

Andrew D. Shore

SmithKline Beecham Pharm., Collegeville, PA 19426, USA

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R. Curtis Haltiwanger

R. Curtis Haltiwanger

SmithKline Beecham Pharm., Collegeville, PA 19426, USA

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First published: 23 May 2010

Abstract

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ChemInform Abstract

An unusual rearrangement/elimination reaction of an azetidin-2-one (I) to a [1,4]-diazapinedione system under mild base-mediated conditions is discovered. A plausible mechanistic pathway is proposed.

chemical structure image

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