Dedicated to Professor Heribert Offermanns on the occasion of his 75th birthday
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Full Paper
Access to a Wide Range of Sultams by Cyclodialkylation of α-Substituted Methanesulfonanilides†
Article first published online: 3 AUG 2012
DOI: 10.1002/ejoc.201200670
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Rassadin, V. A., Grosheva, D. S., Arefeva, I. A., Tomashevskiy, A. A., Sokolov, V. V. and de Meijere, A. (2012), Access to a Wide Range of Sultams by Cyclodialkylation of α-Substituted Methanesulfonanilides . Eur. J. Org. Chem., 2012: 5028–5037. doi: 10.1002/ejoc.201200670
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Publication History
- Issue published online: 3 SEP 2012
- Article first published online: 3 AUG 2012
- Manuscript Received: 17 MAY 2012
Funded by
- Land Niedersachsen
- KAdem CustomChem. GmbH, Göttingen
- German Academic Exchange Service (DAAD)
Keywords:
- Synthetic methods;
- Heterocycles;
- Sulfonamides;
- Cyclodialkylation;
- Substituent effects
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).