Reactivity of Azasydnones: Unusual Diversity in Reactions of Chloro‐ and Nitrophenyl Derivatives with Nitrogen Nucleophiles

Abstract

AbstractReaction with nucleophiles of a range of 3‐arylazasydnones bearing chloro and nitro substituents at the various positons at the phenyl ring using ammonia, primary and secondary amines and azide ion has been assessed in order to develop methodology for the synthesis of corresponding aminophenyl azasydnone derivatives. It has been shown that a nitrogen nucleophile can cause (i) an SNAr reaction when a halogen or the azasydnone moiety itself can be a leaving group; (ii) the azasydnone ring‐opening leading to the formation of aryl azides or azocarboxamides. The observed reactivity of the substrates is discussed in the context of the substituent effect and the nature of the nucleophile.