Synthesis of isoquinolines and pyridines by the palladium-catalyzed iminoannulation of internal alkynes

KR Roesch, H Zhang, RC Larock

Index: Roesch, Kevin R.; Zhang, Haiming; Larock, Richard C. Journal of Organic Chemistry, 2001 , vol. 66, # 24 p. 8042 - 8051

Full Text: HTML

Citation Number: 157

Abstract

A wide variety of substituted isoquinoline, tetrahydroisoquinoline, 5, 6-dihydrobenz [f] isoquinoline, pyrindine, and pyridine heterocycles have been prepared in good to excellent yields via annulation of internal acetylenes with the tert-butylimines of o-iodobenzaldehydes and 3-halo-2-alkenals in the presence of a palladium catalyst. The best results are obtained by employing 5 mol% of Pd (OAc) 2, an excess of the alkyne, 1 equiv of Na2CO3 as a ...