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.

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

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

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