The effects of various acids on the intramolecular cyclization of haplophyllidine (1) were studied. Compound 1 was converted at room temperature by H2SO4, HNO3, HClO4, and a nitrating mixture into anhydroperforine (2) whereas AcOH and HCl (35%) did not affect 1. Nitration of 1 and 2 at 65–70°C led to elimination of MeOH followed by aromatization of ring A and nitration of the furan ring to form 7-methoxy-3,3-dimethyl-9-nitro-2,3-dihydro-1H-furo[2,3-b]pyrano[2,3-h] quinoline (3) and 7-methoxy-3,3-dimethyl-9-nitro-2,3,8,9-tetrahydro-1H-furo[2,3-b]pyrano[2,3-h]quinolin-8-ol (4). Use of Ac2O and HNO3 gave 4,8-dimethoxy-8-(3-methylbut-2-en-1-yl)-5,6,7,8-tetrahydro-furo[2,3-b]quinolin-7-yl nitrate (5). The structures of the synthesized compounds were elucidated using 1D and 2D NMR spectral data, X-ray crystal structure analyses, and DFT quantum chemical methods in the B3LYP/6-31g(d) approximation to calculate the UV and circular dichroism (ECD) spectra of 4.
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Translated from Khimiya Prirodnykh Soedinenii, No. 1, January–February, 2024, pp. 101–108.
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Ubaidullaev, A.U., Zhurakulov, S.N., Vinogradova, V.I. et al. Action of Nitrating Mixtures and Mineral Acids on the Quinoline Alkaloids Haplophyllidine and Anhydroperforine. Chem Nat Compd 60, 119–126 (2024). https://doi.org/10.1007/s10600-024-04265-y
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DOI: https://doi.org/10.1007/s10600-024-04265-y