349130-40-1Relevant academic research and scientific papers
Access to a wide range of sultams by cyclodialkylation of α-substituted methanesulfonanilides
Rassadin, Valentin A.,Grosheva, Daria S.,Arefeva, Irina A.,Tomashevskiy, Aleksandr A.,Sokolov, Victor V.,De Meijere, Armin
, p. 5028 - 5037,10 (2012)
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). The intermolecular cyclodialkylation of α-substituted methanesulfonamides constitutes a simple and efficient route to five- and six-membered sultams with α-ethoxycarbonyl-α-methyl or α-aryl substitution. The intramolecular cyclodialkylation of N-(2,3-dibromopropyl)-α- toluenesulfanilides readily leads to bicyclic sultams bearing a cyclopropane ring. Copyright
