Access to a Wide Range of Sultams by Cyclodialkylation of α-Substituted Methanesulfonanilides
| Autor: | Valentin A. Rassadin, Irina A. Arefeva, Aleksandr A. Tomashevskiy, Daria S. Grosheva, Victor V. Sokolov, Armin de Meijere |
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| Rok vydání: | 2012 |
| Předmět: |
Bicyclic molecule
010405 organic chemistry Chemistry Dimethyl sulfoxide Organic Chemistry Substituent chemistry.chemical_element 010402 general chemistry 01 natural sciences Medicinal chemistry 0104 chemical sciences 3. Good health Catalysis Hexane chemistry.chemical_compound Cerium Yield (chemistry) Organic chemistry Physical and Theoretical Chemistry Acetonitrile |
| Zdroj: | European Journal of Organic Chemistry. 2012:5028-5037 |
| ISSN: | 1434-193X |
| DOI: | 10.1002/ejoc.201200670 |
| Popis: | 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). |
| Databáze: | OpenAIRE |
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