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.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 798–812, May, 2013.
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Zubkov, F.I., Zaytsev, V.P., Obushak, M.D. et al. Synthesis of Epoxyisoindolo[1,2-a]isoquinolinium Salts by an Intramolecular [2+4] Cycloaddition Reaction in 2-Allyl-1-furylisoquinolinium Halides. Chem Heterocycl Comp 49, 746–759 (2013). https://doi.org/10.1007/s10593-013-1306-1
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DOI: https://doi.org/10.1007/s10593-013-1306-1