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N ‐Aryl‐ O ‐acylhydroxylamines: Preparation by O ‐Acylation or N → O Transacylation and Reaction with Amines; Model Reactions for Key Steps Connected with the Carcinogenicity of Aromatic Amines

1988; Wiley; Volume: 27; Issue: 7 Linguagem: Inglês

10.1002/anie.198809731

1521-3773

Gernot Boche, Ferdinand Bosold, Stefan Schröder,

Click Chemistry and Applications

That aromatic amines Aryl‐NH 2 are carcinogenic is (more or less) common knowledge nowadays. N ‐Aryl‐ O ‐acetylhydroxylamines 2 , which are active metabolites thereby, and other O ‐acylhydroxylamines of this type have now been prepared by O ‐acylation of arylhydroxylamines or by transacylation from the hydroxamine acids 1. The compounds 2 react in vitro as electrophilic aminating reagents with amines as nucleophiles to give hydrazines 3. 2 could react analogously in vivo with binucleophiles like DNA. equation image