Access to a Wide Range of Sultams by Cyclodialkylation of α‐Substituted Methanesulfonanilides

Abstract

Abstract A wide range of five‐ and six‐membered sultams bearing an α‐ethoxycarbonyl‐α‐methyl substituent or an α‐aryl group (17 examples) were synthesized by the cyclodialkylation of α‐substituted methanesulfonanilides with α,ω‐dihaloalkanes in the presence of K 2 CO 3 or under phase‐transfer catalysis (PTC) conditions. Upon treatment with K 2 CO 3 in N , N ‐dimethylformamide (DMF) or NaH in dimethyl sulfoxide (DMSO), N ‐(2,3‐dibromopropyl)‐α‐toluenesulfonanilides furnished different 1,3‐diaryl‐2‐thia‐3‐azabicyclo[3.1.0]hexane 2,2‐dioxides in good to excellent yields (51–88 %, 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 (71–84 % yield, 6 examples).