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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
Author(s) -
Boche Gernot,
Bosold Ferdinand,
Schröder Stefan
Publication year - 1988
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.198809731
Subject(s) - acylation , chemistry , nucleophile , electrophile , aryl , reagent , carcinogen , stereochemistry , organic chemistry , medicinal chemistry , alkyl , catalysis
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.