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Synthesis 2005(11): 1859-1875  
DOI: 10.1055/s-2005-869948
PAPER
© Georg Thieme Verlag Stuttgart · New York

Novel Approach to Isoindolo[2,1-a]quinolines: Synthesis of 1- and 3-Halo-Substituted 11-Oxo-5,6,6a,11-tetrahydroisoindolo[2,1-a]quinoline-10-carboxylic Acids

Ekaterina V. Boltukhina, Fedor I. Zubkov*, Eugenia V. Nikitina, Alexey V. Varlamov
Organic Chemistry Department of Russian People’s Friendship University, 6, Miklukho-Maklayia St., Moscow 117198, Russian Federation
Fax: +7(095)9550779; e-Mail: fzubkov@sci.pfu.edu.ru;
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Publication History

Received 2 November 2004
Publication Date:
20 June 2005 (online)

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Abstract

A series of 1- and 3-halo-substituted isoindolo[2,1-a]quinolines were obtained by means of electrophilic cyclization of methallyl- and allyl-substituted isoindolo-7-carboxylic acids. The influence of halogen atoms on the stereochemistry of the formation of key intermediates, 3a,6-epoxyisoindoles, was studied.

Key words

furans - intramolecular Diels-Alder reactions - cyclizations - electrophilic aromatic substitutions - isoindolo[2,1-a]quinolines