Synthesis 2005(7): 1069-1076  
DOI: 10.1055/s-2005-861832
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Pyrrolo- and Pyrido-[1,2-a]benzimidazolequinone Anti-tumor Agents Containing a Fused Cyclopropane Ring

John O’Shaughnessy, Fawaz Aldabbagh*
Department of Chemistry, National University of Ireland, Galway, Ireland
Fax: +353(91)525700; e-Mail: Fawaz.Aldabbagh@nuigalway.i.e;
Further Information

Publication History

Received 6 December 2004
Publication Date:
21 February 2005 (eFirst)

Abstract

A cyclopropane ring has been fused onto tetrahydropyrrolo- and tetrahydropyrido-[1,2-a]-benzimidazoles and -benzimidazolequinones via the cycloaddition of diazomethines generated from the thermolysis of N-(allyl and but-3-enyl)benzimidazole-2-Eschenmoser hydrazones (aziridinyl imines). At lower temperatures, the 1,3-dipolar [3 + 2] cycloadduct was obtained for only the N-allylbenzimidazole-2-Eschenmoser hydrazones.

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