The title compound, C17H18NO+·I−, is an adduct resulting from an intramolecular Diels–Alder reaction of methallyl chloride with 3,4-dihydro-1-furylisoquinoline. The cation comprises a fused pentacyclic system containing three five-membered rings (dihydropyrrole, dihydrofuran and tetrahydrofuran) and two six-membered rings (tetrahydropyridine and benzene). The five-membered rings have the usual envelope conformations, and the central six-membered tetrahydropyridine ring adopts the unsymmetrical half-boat conformation. In the crystal, cations and iodide anions are bound by weak intermolecular hydrogen-bonding interactions into a three-dimensional framework.
2-a]isoquinoline Core of the Jamtine and Hirsutine Alkaloids. -N-Alkylation of isoquinoline derivatives with alkyl halides affords intermediate iminium salts, which undergo unexpected spontaneous intramolecular Diels-Alder reaction to produce cycloadducts with the basic structural core of the title alkaloids. -(ZUBKOV*, F. I.; ERSHOVA, J. D.; ZAYTSEV, V. P.; OBUSHAK, M. D.; MATIYCHUK, V. S.; SOKOLOVA, E. A.; KHRUSTALEV, V. N.; VARLAMOV, A. V.; Tetrahedron Lett. 51 (2010) 52, 6822-6824, http://dx.
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