O-alkylation chemistry of neocupferron

O-Alkylation of N-hydroxy-N-nitroso-1-naphthalenamine ammonium salt (neocup ferron) leads to two isomers, (1,4) naphthoquinone O-alkyl oxime oxime (A) and N-alkyloxy-N'-naphthyldiimide N'-oxide (B). Characterization was done b y H-1,C-13 NMR and X-ray analysis. These derivatives showed increased stabi lity compared to their parent compound, neocupferron, in the ability to rel ease nitric oxide (NO). Some of these O-alkyl derivatives can be novel phot o-releasing NO compounds. (C) 2000 Elsevier Science Ltd. All rights reserve d.