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Synthesis 2012(2): 253-258  
DOI: 10.1055/s-0031-1289967
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

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

Mayavan Viji, Rajagopal Nagarajan*
School of Chemistry, University of Hyderabad, Hyderabad 500 046, India
e-Mail: rnsc@uohyd.ernet.in;
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Publikationsverlauf

Received 20 October 2011
Publikationsdatum:
20. Dezember 2011 (online)

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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.

Key words

Povarov reaction - annulations - heterocycles - Lewis acids­ - regioselectivity

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18

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.