Rassadin, Valentin A.Valentin A.RassadinGrosheva, Daria S.Daria S.GroshevaArefeva, Irina A.Irina A.ArefevaTomashevskiy, Alexander A.Alexander A.TomashevskiySokolov, Viktor V.Viktor V.Sokolovde Meijere, ArminArminde Meijere2018-11-072018-11-072012https://resolver.sub.uni-goettingen.de/purl?gro-2/25627A wide range of five- and six-membered sultams bearing an a-ethoxycarbonyl-a-methyl substituent or an a-aryl group (17 examples) were synthesized by the cyclodialkylation of a-substituted methanesulfonanilides with a,?-dihaloalkanes in the presence of K2CO3 or under phase-transfer catalysis (PTC) conditions. Upon treatment with K2CO3 in N,N-dimethylformamide (DMF) or NaH in dimethyl sulfoxide (DMSO), N-(2,3-dibromopropyl)-a-toluenesulfonanilides furnished different 1,3-diaryl-2-thia-3-azabicyclo[3.1.0]hexane 2,2-dioxides in good to excellent yields (5188?%, 16 examples). The 4-methoxyphenyl (PMP) group was easily removed from the sultam nitrogen atom by treatment of the corresponding bicyclic sultams with cerium(IV) ammonium nitrate in acetonitrile (7184?% yield, 6 examples).journal_article10.1002/ejoc.201200670000308294700021