1990 年 38 巻 5 号 p. 1373-1378
N1-Tosyl-N1, N2-diarylacetamidine (1) suffered nucleophilic attack of N-tosylamines and N-acylamines at the amidine central carbon to give N1-tosyl and N1-acyl derivatives of N-1, N2-disubstituted acetamidine in the presence of a basic catalyst.Preparation of N1-(p-nitrobenzenesulfonyl)-N1, N2-diarylacetamidines (8) was attempted to obtain better starting materials for the above amide exchange reaction. These compounds, however, proved to be unsuitable for the purpose because they readily underwent Smiles rearrangement to give N1-(p-nitrophenyl-N1, N2-diarylacetamidines (9) with loss of sulfur dioxide.N1-(p-Nitrophenyl)-N1-(p-methylphenyl)-N2-(p-chlorophenyl)acetamidine (9d) was formed when an ethanol solution of N1-(p-nitrobenzenesulfonyl)-N1-(p-chlorophenyl)-N2-(p-methylphenyl)acetamidine (8d) was refluxed for 2.5h in the absence of any catalyst.
