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Access to a Wide Range of Sultams by Cyclodialkylation of α‐Substituted Methanesulfonanilides
Author(s) -
Rassadin Valentin A.,
Grosheva Daria S.,
Arefeva Irina A.,
Tomashevskiy Aleksandr A.,
Sokolov Victor V.,
de Meijere Armin
Publication year - 2012
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201200670
Subject(s) - chemistry , cerium , substituent , aryl , yield (engineering) , medicinal chemistry , acetonitrile , bicyclic molecule , dimethylformamide , ammonium nitrate , catalysis , sulfoxide , dimethyl sulfoxide , organic chemistry , combinatorial chemistry , solvent , alkyl , materials science , metallurgy
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).