Abstract
An efficient and convenient synthesis of pyrazolo[5,1-a]isoquinolines has been achieved via palladium-catalyzed Sonogashira coupling of terminal alkynes with 5-(2-bromophenyl)-1H-pyrazoles, in situ formed from the condensation of 1-(2-bromophenyl)buta-2,3-dien-1-ones with hydrazine hydrate, followed by 6-endo intramolecular alkyne hydroamination. More interestingly, 8-methylenepyrazolo[5,1-a]isoindoles, the regioisomer of pyrazolo[5,1-a]isoquinolines, could also be selectively synthesized from the same starting materials through an initial intermolecular hydroamination of terminal alkynes with 5-(2-bromophenyl)-1H-pyrazoles followed by a palladium-catalyzed 5-exo intramolecular Heck coupling reaction.
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