Two new methods for 2,3-Pyridyne formation

The compounds 2-chloro-4-methoxypyridine and 4-methoxy-2-trifluoromethylsulfonyloxy-3-trimethylsilylpyridine were shown to be relatively efficient precursors for 4-methoxy-2,3-pyridyne as was evidenced by its trapping with furan, 2-methylfuran and 2-methoxyfuran. These findings constitute the first published report of the use of either directed-deprotonation or fluoride-induced elimination to prepare the reactive 2,3-pyridyne intermediate.