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- Title
Access to a Wide Range of Sultams by Cyclodialkylation of α-Substituted Methanesulfonanilides.
- Authors
Rassadin, Valentin A.; Grosheva, Daria S.; Arefeva, Irina A.; Tomashevskiy, Aleksandr A.; Sokolov, Victor V.; de Meijere, Armin
- 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 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)-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).
- Publication
European Journal of Organic Chemistry, 2012, Vol 2012, Issue 26, p5028
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201200670