reactions of pentafluoropyridine with amidoximes

In this paper, site reactivity of amidoximes with pentafluoropyridine under basic conditions in dry ch3cn was investigated. the aromatic nucleophilic substitution of pentafluoropyridine with amidoximes occurs in the 4-position of the pyridine ring by the oxygen site of amidoximes and followed by reaction of other sites, depending on reaction conditions. substituted imidamide systems 4a–g were readily accessed using a 1:1 molar ratio of pentafluoropyridine and amidoximes in concentrated acetonitrile and in reflux condition for 6 h, while reaction of pentafluoropyridine with amidoximes in 1:1 molar ratio and in diluted acetonitrile under reflux condition for 24 h gave novel pyridooxadiazine system 4h, i. pentafluoropyridine reacts also with amidoximes in 2:1 molar ratio under dry conditions to afford the bis-perfluoropyridyl imidamide systems 4j, k.