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Novel Method for the Synthesis of 3-Monosubstituted Six-membered Benzosultams

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  To develop an efficient method for the construction of 3-monosubstituted six-membered benzosultams,especially for the synthesis of 3-arylated analogues.Method: 3-Monosubstituted six-membered benzosultams with a wide range of functional groups were prepared by simple and convenient two-step procedures.OLithiation of N-Boc-o-toluenesulfonamide followed by reaction with aldehydes gave carbinol sulfonamides,which were converted to 3-monosubstituted six-membered benzosultams via TMSCl/NaI/MeCN reagent mediated cyclization.Results:The method is especially effective for the preparation of 3-monoarylated benzosultams.But for the bulky aliphatic substituents like cyclohexyl and tert-butyl,the yields are less than satisfactory even for an extended reaction time(10 h).Conclusion:A new synthetic approach for the facile preparation of the 3-monosubstituted six-membered benzosultams is developed via the novel cyclization mediated by TMSCl/Nal/MeCN reagent.The mechanism,scope and limitations of this novel transformation is also elucidated.……