Synthesis of Pyridoisoindoles through Diazotization Followed by Intramolecular Cyclization from Pyridinylarylacetates in One Pot

초록

A robust synthetic method for a variety of pyridoisoindoles from pyridinylarylacetates has been developed through diazotization using 4-methylbenzenesulfonyl azide and 1,8-diazabicyclo[5.4.0]undec-7-ene followed by intramolecular cyclization via elimination of a nitrogen molecule under copper(II) trifluoromethanesulfonate-catalyzed conditions in a one-pot process. The intramolecular cyclization also took place efficiently with diazo substrates to produce pyridoisoindoles in good to excellent yields under metal-free conditions or catalytic conditions [1.0 mol% copper(II) trifluoromethanesulfonate, 25 degrees C].

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