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Access to a Wide Range of Sultams by Cyclodialkylation of alpha-Substituted Methanesulfonanilides

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dc.bibliographiccitation.firstpage5028
dc.bibliographiccitation.issue26
dc.bibliographiccitation.journalEuropean Journal of Organic Chemistry
dc.bibliographiccitation.lastpage5037
dc.contributor.authorRassadin, Valentin A.
dc.contributor.authorGrosheva, Daria S.
dc.contributor.authorArefeva, Irina A.
dc.contributor.authorTomashevskiy, Alexander A.
dc.contributor.authorSokolov, Viktor V.
dc.contributor.authorde Meijere, Armin
dc.date.accessioned2018-11-07T09:06:46Z
dc.date.available2018-11-07T09:06:46Z
dc.date.issued2012
dc.description.abstractA 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).
dc.identifier.doi10.1002/ejoc.201200670
dc.identifier.isi000308294700021
dc.identifier.urihttps://resolver.sub.uni-goettingen.de/purl?gro-2/25627
dc.notes.statuszu prüfen
dc.notes.submitterNajko
dc.publisherWiley-v C H Verlag Gmbh
dc.relation.issn1434-193X
dc.titleAccess to a Wide Range of Sultams by Cyclodialkylation of alpha-Substituted Methanesulfonanilides
dc.typejournal_article
dc.type.internalPublicationyes
dc.type.peerReviewedyes
dc.type.statuspublished
dspace.entity.typePublication

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