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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 36, 2006 - Issue 3
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Original Articles

Synthesis of Tetrahydrobenzazepinesulfonamides and Their Rearrangement to Diarylsulfones

Hui Ren Department of Chemistry & Biochemistry, University of the Sciences in Philadelphia, Philadelphia, Pennsylvania, USA
,
Murray Zanger Department of Chemistry & Biochemistry, University of the Sciences in Philadelphia, Philadelphia, Pennsylvania, USACorrespondence[email protected]
&
James R. McKee Department of Chemistry & Biochemistry, University of the Sciences in Philadelphia, Philadelphia, Pennsylvania, USA
Pages 355-363 | Received 28 Jul 2005, Published online: 19 Aug 2006
 
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Abstract

A new class of diarylsulfones, in which tetrahydrobenzazepine comprises one of the aromatic moieties, has been synthesized via the acid‐catalyzed rearrangement of several substituted benzazepinesulfonamides. The rearrangement is normally ortho but in at least one case a para isomer is also formed. Sulfones of this type have been shown to possess potent anti‐HIV activity.

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