53269-36-6Relevant articles and documents
Cine substitution in reaction of unactivated 2-halopyridines with 2-aminopyridine 1-oxide. Formation of 3-(2-pyridylamino)-2(1H)-pyridone [1]
Rykowski,Pucko
, p. 2378 - 2383 (2007/10/03)
Reaction of 2-aminopyridine 1-oxide 1a with2-fluoropyridine 5a in DMF at 140°C gave 2-(2-pyridylamino)pyridine 1-oxide 6 (41%) along with bis(2-pyridyl)amine 7 (5%). However, heating in melt of 1a with 2-chloropyridine 5b or 2-bromopyridine 5c in the presence of dry potassium carbonate at 175°C provided 3-(2-pyridylamino)-2(1H)-pyridone 9 as cine substitution product. Compound 9 results from the nucleophilic attack of the N-oxide on the carbon atom bearing halogen to give corresponding cation 17, which rearranges to cine substitution product 9 via anhydro-base 18.