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MICROWAVE-ASSISTED SEQUENTIAL THREE-COMPONENT SYNTHESIS OF PYRROLYL-SUBSTITUTED CHROMENO[2,3-c]ISOQUINOLIN-5-AMINES

Xiaoyi Yue, Olga A. Storozhenko, Alexey A. Festa, Elena A. Sorokina, Alexey A. Varlamov, Leonid G. Voskressensky
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Abstract


Sequential one-pot domino reaction of homophthalonitrile, salicylaldehydes, and pyrroles in basic media under MW irradiation results in the formation of novel chromeno[2,3-c]isoquinolin-5-amines. The transformation represents a domino sequence that starts with Knoevenagel condensation, followed by two nucleophilic cyclizations, consecutively forming 2-iminochromene and 5-iminoisoquinoline cycles. Michael addition of the pyrrole unit to the chromene cycle finishes the transformation. The reaction tolerates various salicylaldehydes and pyrroles, producing target molecules with good 45–67% yields.

Keywords


2-aminochromene; isoquinolin-5-amines; salicylaldehyde; domino reaction; multicomponent reaction.

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