Summary.
Isoquinolin-1-ylmethylfuranones could be readily prepared from certain Reissert-compounds and isopilopyl bromide by standard procedures. Their reduction to the desired not isolated 1,2,3,4-tetrahydroisoquinoline intermediates was achieved by chemical and/or catalytical hydrogenation, followed by intramolecular amidation conveniently giving the title compounds in a one-pot synthesis. The structures and the stereochemistry of the target compounds were assigned by 13C NMR spectroscopy and X-ray diffraction analysis.
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The second author is part of PhD thesis, LMU München, Germany
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Reimann, E., Renz, M. & Polborn, K. Synthesis of cis-2,3-Disubstituted Benzo[a]quinolizidin-4-ones via Reissert-Compounds. Monatsh. Chem. 137, 1411–1419 (2006). https://doi.org/10.1007/s00706-006-0540-y
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DOI: https://doi.org/10.1007/s00706-006-0540-y