Volume 33, Issue 8
Isocyclic Compounds
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ChemInform Abstract: Cleavage of the N(1)—C(4) Bond of 4-(4′-Hydroxyphenyl)-azetidine-2-ones via Quinone Methide Intermediates.

Larry A. Cabell

Larry A. Cabell

Dep. Neuro-Oncol., M. D. Anderson Cancer Cent., Univ. Tex., Houston, TX 77030, USA

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Loren W. Hedrich

Loren W. Hedrich

Dep. Neuro-Oncol., M. D. Anderson Cancer Cent., Univ. Tex., Houston, TX 77030, USA

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John S. McMurray

John S. McMurray

Dep. Neuro-Oncol., M. D. Anderson Cancer Cent., Univ. Tex., Houston, TX 77030, USA

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First published: 22 May 2010

Abstract

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ChemInform Abstract

On treatment with base, azetidinones (I) undergo a novel ring-opening reaction to give quinone methide intermediates. Their 1,6-conjugate addition reactions yield the esters (III) and (V).

chemical structure image

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