Synthesis of cyclic sulfonamides through intramolecular Diels-Alder reactions

[GRAPHICS] 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-sulionic 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 H-3 receptor antagonist.