Efficient synthesis of N-substituted lactams from (N-arylsulfonyloxy) amines and cyclic ketones

RV Hoffman, JM Salvador

Index: Hoffman, Robert V.; Salvador, James M. Tetrahedron Letters, 1989 , vol. 30, # 32 p. 4207 - 4210

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Citation Number: 19

Abstract

A new method is reported for the direct preparation of N-substituted lactams from cycloalkanones. N-(p-nitrobenzenesulfonoxyl) methylamine (CH 3 NH-OSO 2 C 6 H 4 NO 2 ) was reacted with a series of cycloalkanones to give good yields of N-methyl lactams. An addition-rearrangement pathway accounts for the ring-expanded lactam products. A series of N-alkyl-N-arylsulfonoxyl amines were generated in situ and reacted with cyclobutanone ...