Condensed heteroaromatic ring systems. VII Synthesis of thienopyridines, thienopyrimidines, and furopyridines from o-substituted N-heteroarylacetylenes.

the cross-coupling reaction of 2-chloro-3-iodo- and 4-chloro-3-iodopyridines with phenylacetylene in the presence of dichlorobis(triphenylphosphine)palladium occurred at the 3-position. The 3-ethynylpyridines containing an adjacent chloro group were convertible to thienopyridines by traatment with sodium hydrosulfide. Similarly, various thieno[2, 3-d]pyrimidines were synthesized from 4-chloro-5-iodopuyrimidines. One-step synthesis of furopyridines by the palladium-catalyzed reaction of iodohydroxypyridines with terminal acetylenes is also described.