SYNTHESIS OF EPOXYISOINDOLO[1,2-<i>a</i>]ISOQUINOLINIUM SALTS BY AN INTRAMOLECULAR [2+4] CYCLOADDITION REACTION IN 2-ALLYL-1-FURYLISOQUINOLINIUM HALIDES
DOI:
https://doi.org/10.1007/151Keywords:
alkaloids, allyl halides, furan, isoindolo[1, 2-a]isoquinolines, intramolecular [2 4] cycloadditionAbstract
We examined the tandem alkylation/[2+4] cycloaddition of 1-(2-furyl)-3,4-dihydroisoquinolines by various allyl halides. It was found that the process occurred through the intermediate formation of 2-allyl-1-furyl-3,4-dihydroisoquinolinium salts with a subsequent intramolecular exo addition of the allyl fragment to the furan ring. The adducts obtained were structural analogs of the isoindolo[1,2-a]isoquinoline alkaloids jamtine and hirsutine.
Authors: F. I. Zubkov, V. P. Zaytsev, M. D. Obushak, Yu. D. Ershova, D. F. Mertsalov, E. A. Sorokina, E. V. Nikitina, Yu. I. Gorak, R. Z. Lytvyn, and A. V. Varlamov
English Translation in Chemistry of Heterocyclic Compounds, 2013, 49 (5), pp 746-759