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Synthesis 2009(24): 4219-4225  
DOI: 10.1055/s-0029-1217049
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Convenient Procedure for the Synthesis of New α-Pyridinyl-Substituted 7H-Indeno[2,1-c]quinoline Derivatives Based on a Three-Component Imino Diels-Alder Reaction

Vladimir V. Kouznetsov*a, Arnold R. Romero Bohórqueza, Luis Astudillo Saavedrab
a Laboratorio de Química Orgánica y Biomolecular, Escuela de Química, Universidad Industrial de Santander, A.A. 678, Bucaramanga, Colombia
Fax: +57(76)349069; e-Mail: kouznet@uis.edu.co;
b Instituto de Química de Recursos Naturales, Universidad de Talca, Casilla: 747, Talca, Chile
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Publication History

Received 17 June 2009
Publication Date:
19 October 2009 (online)

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Abstract

A new series of α-pyridinyl-substituted indeno[2,1-c]quinoline derivatives was prepared with good yields according to a two-step synthesis. The first and key step involves the formation of the ring via three-component imino Diels-Alder cycloaddition between an aniline, pyridine-2-carbaldehyde, and indene using boron trifluoride-diethyl ether complex as a catalyst to produce the corresponding 5,6,6a,11b-tetrahydroindeno[2,1-c]quinolines. The second step consisted of their oxidation with powdered sulfur to obtain the corresponding indeno[2,1-c]quinolines, analogues of DNA topoisomerase inhibitor TAS-103.

Key words

cycloaddition - multicomponent reaction - imino Diels-Alder reaction - indeno[2,1-c]quinolines

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22

Full crystallographic data for indenoquinoline 7c will be published elsewhere.

23

Another commonly used oxidant, DDQ in MeCN, was less efficient for this process due poor solubility of the starting tetrahydroindeno[2,1-c]quinolines.

24

Antitumoral and cytotoxic activities for this new series of compounds will be published in due course.