CAN-Catalyzed Regioselective Synthesis of Pyrido[2,3-c]carbazoles by the Povarov Reaction

Abstract

A simple route for the synthesis of 3-methyl-3H-pyrido[2,3-c]carbazoles via Povarov reaction of 3-aminocarbazoles, and ethyl vinyl ether is described. This transformation, catalyzed by cerium(IV) ammonium nitrate (CAN) under mild reaction conditions, provides the pyrido[2,3-c]carbazoles in good yields with high regioselectivity.

Povarov reaction - annulations - heterocycles - Lewis acids­ - regioselectivity

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<A NAME="RZ99011SS-18">18</A>

The CCDC deposition number for compound 3g is 845183; molecular formula: C₂₃H₁₈N₂. Chemical formula weight is 322.39; orthorhombic; unit cell parameters: a = 6.6003(8) Å, b = 18.947(3) Å, c = 27.539(4) Å, α = β = γ = 90˚. Space group Pbca.