Tetrahedron letters

A simple, one-flask transformation of ketones to N-methyl lactams

RV Hoffman, JM Salvador

Index: Hoffman, Robert V.; Salvador, James M. Tetrahedron Letters, 1991 , vol. 32, # 22 p. 2429 - 2432

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Citation Number: 11

Abstract

Abstract A one-flask conversion of cyclic ketones to N-methyl lactams is described. Reaction of the ketone with triethylorthoformate generates an acetal which is reacted in situ with N-(((p- nitrobenzene) sulfonyl) oxy methylamine 2a (CH 3 NH-OSO 2 C 6 H 4 NO 2). Dealkylation of the resulting O-ethyl imidate with sodium iodide gives the lactam. A variety of lactams, including macrocyclic lactams, are produced simply and in good yields.

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