Amidines. V. : Smiles Rearrangement of N^1-(p-Nitrobenzenesulfonyl)-N^1,N^2-diarylacetamidines

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概要

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• N^1-Tosyl-N^1,N^2-diarylacetamidine (1) suffered nucleophilic attack of N-tosylamines and N-acylamines at the amidine central carbon to give N^1-tosyl and N^1-acyl derivatives of N-1,N^2-disubstituted acetamidine in the presence of a basic catalyst.Preparation of N^1-(p-nitrobenzenesulfonyl)-N^1,N^2-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 N^1-(p-nitrophenyl-N^1,N^2-diarylacetamidines (9) with loss of sulfur dioxide.N^1-(p-Nitrophenyl)-N^1-(p-methylphenyl)-N^2-(p-chlorophenyl)acetamidine (9d) was formed when an ethanol solution of N^1-(p-nitrobenzenesulfonyl)-N^1-(p-chlorophenyl)-N^2-(p-methylphenyl)acetamidine (8d) was refluxed for 2.5h in the absence of any catalyst.

• 社団法人日本薬学会の論文
• 1990-05-25

著者

• 尾能 満智子

  東邦大薬

• 尾能 満智子

  School Of Pharmaceutical Sciences Toho University

• 田村 眞造

  School of Pharmaceutical Sciences, Toho University

• 荒谷 一郎

  School of Pharmaceutical Sciences, Toho University

• 田村 眞造

  School Of Pharmaceutical Sciences Toho University

• 田村 真造

  東邦大学 薬

• 荒谷 一郎

  School Of Pharmaceutical Sciences Toho University

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