Synthesis of cyclic sulfonamides through intramolecular Diels-Alder reactions.
[figure: see text] 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.
Greig
I R
IR
James Black Foundation, 68 Half Moon Lane, Dulwich, London, SE24 9JE, UK. matthew.tozer@kcl.ac.uk
Tozer
M J
MJ
Wright
P T
PT
D018360:Crystallography, X-Ray; D006633:Histamine Antagonists / Q000138:chemical synthesis; D009682:Magnetic Resonance Spectroscopy; D018100:Receptors, Histamine H3 / Q000187:drug effects; D013449:Sulfonamides / Q000138:chemical synthesis* / Q000737:chemistry
D006633:Histamine Antagonists; D018100:Receptors, Histamine H3; D013449:Sulfonamides