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Synfacts 2007(6): 0580-0580  
DOI: 10.1055/s-2007-968575
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York

Highly Regioselective Synthesis of Furoquinoline Derivatives

Contributor(s): Victor Snieckus, Todd Macklin
Z. Zhang, Q. Zhang, S. Sun, T. Xiong, Q. Liu*
Northeast Normal University, Changchun, P. R. of China
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Publication History

Publication Date:
22 May 2007 (online)

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Significance

Reported is a tin(IV) chloride mediated tandem ring opening/recyclization of readily available doubly activated cyclopropanes which leads to fused quinolines in moderate to excellent yields. The reaction is limited to activated anilines and gives products with high chemo- and regio­selectivity. Several key intermediates were characterized and a mechanism was proposed involving tin(IV) chloride mediated dihydrofuran ring generation followed by a Combes-type annulation which involves the essential participation of water (R. Lang, K. Schofield J. Chem. Soc. 1953, 3161-3167).