Synthesis of isoquinolines through the coupling of Fischer carbene complexes with o-alkynylpyridine carbonyl derivatives

The reaction of Fischer carbene complex with o-alkynylpyridine carbonyl derivatives has been investigated. This involves the generation of furo[3,4-c]pyridine as transient intermediates through the coupling of o-alkynylpyridine carbonyl derivatives with carbene complex and subsequent Diels–Alder trapping with suitable dienophiles resulted in the formation of isoquinoline derivatives and the entire sequence can be run in one pot. When an olefinic tether was present, intramolecular Diels–Alder cycloaddition occurred followed by ring opening to yield tricyclic alcohols.

Graphical abstractThe reaction of Fischer carbene complex with o-alkynylpyridine carbonyl derivatives has been investigated. The reaction initially affords furo[3,4-c]pyridine as transient intermediates, which can be trapped by suitable dienophiles to afford isoquinoline derivatives.Figure optionsDownload full-size imageDownload as PowerPoint slide