A Convenient Synthesis of Pyrrolo[3,4-c]quinolines

Andrea Virányi; Miklós Nyerges; Gábor Blaskó; László Tőke

doi:10.1055/s-2003-42425

PAPER

A Convenient Synthesis of Pyrrolo[3,4-c]quinolines

Andrea Virányi^a, Miklós Nyerges*^a, Gábor Blaskó^b, László Tőke^a
^a Research Group of the Hungarian Academy of Sciences, Department of Organic Chemical Technology, Technical University of Budapest, 1521 Budapest P.O.B. 91, Hungary
^b EGIS Pharmaceuticals Ltd., 1475 Budapest P.O.B. 100, Hungary
Fax: +36(1)4633648; e-Mail: mnyerges@mail.bme.hu;

Abstract

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Abstract

A new route to the pyrrolo[3,4-c]quinoline ring system has been developed. The synthesis proceeds stereoselectively in three steps, using 1,3-dipolar cycloaddition of azomethine ylides as a key step. First, a series of 4-arylpyrrolidine-3-carboxylic acids have been prepared from the appropriate cinnamic esters and a nonstabilized azomethine ylide. The reduction of a nitro group on the aromatic ring was followed by acid-catalyzed intramolecular lactam formation.

Key words

amino acids - cyclizations - cycloaddition - lactams - quinolines

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Referenzen

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