Experimental synthesis demonstrates efficient one-pot production of pyridoisoindoles from pyridinylarylacetates, indicating a practical route to valuable heterocycles.
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 °C]. magnified image
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Kim et al. (2015) studied this question.
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