Abstract
The condensation of 2-amino-3-hydroxypyridine with 2-furoyl chloride according to Ladenburg gave 2-(2-furyl)[1,3]oxazolo[4,5-b]pyridine which was subjected to electrophilic substitution reactions with nitric acid, bromine, hexamethylenetetramine, acetic anhydride, and benzoic acid. In all cases, the electrophile entered exclusively the 5-position in the furan ring. Treatment of the title compound with methyl iodide afforded the corresponding quaternization product at the N4 atom, whereas no Chichibabin amination was observed.
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