W. Verboom, Y. Morzherin, E. Kelderman
Sep 2, 2010
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Journal
Recueil des Travaux Chimiques des Pays-Bas
Abstract
Appropriately 4-substituted 1,2,3,3a,4,5-hexahydro-3a-(methoxymethyl)pyrrolo[1,2-a]quinolines 3 cyclize to 2,3-dihydro-1 H,4H,6H-furo[3,4-b]pyrrolo[1,2-a]quinoline-6a(7H)-carbonitrile (5) upon heating in polar solvents, the reaction being accelerated by lithium bromide. The formation of the annulated tetrahydrofuran ring of 5 takes place via intramolecular attack of the oxygen atom of the methoxymethyl substituent at C-3a on the electrophilic carbon atom at C-4. The structure of 5 was confirmed by single-crystal X-ray structure determination.