Heteroatom rearrangements. S,N, O,N, and N,N double rearrangements. X-Ray molecular structure of 5-cyano-6-methylthio-2,3-diphenyl-pyrimidin-4(3H)-one

Abstract

New heteroatom rearrangements are reported; ‘S,N, O,N, and N,N double rearrangements’ take place when acrylonitriles, substituted at C-3 by two heteroatom groups (MeS or MeSe, and SH, OH, or NHPh), condense with aromatic carboxylic acids in the presence of dehydrating agents such as PPE, PPSE, phosphoryl trichloride, and propylphosphonic acid cyclic anhydride. The key step of this reaction is the acylation of the cyano group of the acrylonitrile, followed by transfer of the heteroatom group (SMe or SeMe).