American Chemical Society
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Synthesis of Cyclic Sulfonamides through Intramolecular Diels−Alder Reactions

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journal contribution
posted on 2001-01-09, 00:00 authored by Ian R. Greig, Matthew J. Tozer, Paul T. Wright
Substituted 2,3,3a,4,5,7a-hexahydrobenzo[d]isothiazole 1,1-dioxides and 3,4,4a,5,6,8a-hexahydro-2H-benzo[e][1,2]thiazine 1,1-dioxides, novel cyclic sulfonamides, were synthesized by the thermal Diels−Alder reaction of triene derivatives of buta-1,3-diene-1-sulfonic acid amide. The stereochemical outcome of the reaction was determined by NMR spectroscopy and X-ray crystallographic analysis. This chemistry has been used for the synthesis of 2-(4-chlorobenzyl)-5-(1H-imidazol-4-yl)-2,3,3a,4,5,7a-hexahydrobenzo[d]isothiazole 1,1-dioxide, a histamine H3 receptor antagonist.