69726-89-2Relevant 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
supporting information, p. 5028 - 5037,10 (2020/08/24)
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
Fluorous-tethered quenching reagents for solution phase parallel synthesis
Lindsley, Craig W.,Zhao, Zhijian,Leister, William H.
, p. 4225 - 4228 (2007/10/03)
Commercially available fluorous-tethered reagents are employed to quench excess reactants and remove known impurities from crude reaction mixtures generated via solution phase parallel synthesis. Fluorous quenching reagents are expediently removed via FluoroFlash SPE columns to afford products in high yields and purities.
Nucleophilic Substitution Reaction of Phenylmethanesulfonyl Halides with Anilines
Lee, Ikchoon,Kang, Han Keun,Lee, Hai Whang
, p. 7472 - 7477 (2007/10/02)
Kinetic studies on the nucleophilic substitution reaction of Y-substituted phenylmethanesulfonyl halides with X-substituted anilines in methanol-acetonitrile have been carried out in order to elucidate the reaction mechanism.The phenylmethanesulfonyl fluorides (PSF) had markedly lower rates and smaller magnitudes of ρX and ρY values compared with those for the chlorides (PSC).On the contrary, however, the magnitude of the cross-interaction constant ρXY was greater for PSF than for PSC, so that the degree of bond making in the transition state is actually greater in the reaction of PSF as compared with that for PSC.We have thus demonstrated that extensive charge transfer from a nucleophile to a substrate does not necessarily mean a tight bond in the transition state.Moreover the nonzero ρXY values obtained for both PSC and PSF are taken as evidence in support of a common, associative SN2 mechanism for the two halides.
