Preparation of N-aryl-2-hydroxypropionamides from hydroxy aromatic compounds using a one-pot smiles rearrangement procedure

JJ Weidner, PM Weintraub, RA Schnettler, NP Peet

Index: Weidner, John J.; Weintraub, Philip M.; Schnettler, Richard A.; Peet, Norton P. Tetrahedron, 1997 , vol. 53, # 18 p. 6303 - 6312

Full Text: HTML

Citation Number: 29

Abstract

Acylation of hydroxy aromatic compounds with 2-bromo-2-methylpropionamide followed by Smiles rearrangement of the resulting 2-aryloxypropionamide in a one-pot procedure produced the corresponding 2-hydroxy-2-methyl-N-arylpropionamides which can be converted to arylamines by hydrolysis. Particularly important applications of this new process were the conversions of estrone (6) and estradiol (14) to the corresponding 3- ...