On the Ritter reaction of cyclic hydroxyamines: Synthesis of conformationally-restricted reduced amide dipeptide isosteres
The Ritter reactions of 3-alkyl-3-hydroxyazetidine or -piperidine derivatives give low yields of the desired products, whereas the 3-alkyl-3-hydroxy-pyrrolidine and 4-alkyl-4-hydroxy-piperidine derivatives react smoothly to give the corresponding acetamides. An alternative route to 3-acylamino-3-alkylpiperidines, which were designed as conformationally-restricted reduced amide dipeptide isosteres, was devised from nipecotic acid vai a Hofmann rearrangement.
Taylor, G. Mark,Baker, Stewart J.,Gedney, Andrea,Pearson, David J.,Sibley, Graham E. M.
p. 1297 - 1300
(2007/10/03)
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