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<p>The action of nitrating mixtures [(HNO<sub>3</sub> + 3H<sub>2</sub>SO<sub>4</sub>), (AcOH + HNO<sub>3</sub>)] on acetylhaplophyllidine was studied. Intramolecular cyclization in two directions to form anhydroperforine (<b>2</b>) and spiro compound <b>3</b> or <b>4</b> and 2-nitrofuranoquinoline <b>5</b> occurred in AcOH. Loss of MeOH and H<sub>2</sub>O molecules occurred under more forcing conditions (HNO<sub>3</sub> + 3H<sub>2</sub>SO<sub>4</sub>) and was accompanied by aromatization of ring D of anhydroperforine to produce compound <b>6</b>. The structures of the obtained compounds were established using 1D and 2D NMR spectroscopy and an X-ray crystal structure analysis.</p>

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Reactions of Acetylhaplophyllidine with Nitrating Mixtures Under Various Conditions

  • 期刊论文

  • 发表日期：

    2025年11月20日

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  • A. U. Ubaydullaev,
  • Sh. N. Zhurakulov,
  • V. I. Vinogradova,
  • K. K. Turgunov

摘要

The action of nitrating mixtures [(HNO3 + 3H2SO4), (AcOH + HNO3)] on acetylhaplophyllidine was studied. Intramolecular cyclization in two directions to form anhydroperforine (2) and spiro compound 3 or 4 and 2-nitrofuranoquinoline 5 occurred in AcOH. Loss of MeOH and H2O molecules occurred under more forcing conditions (HNO3 + 3H2SO4) and was accompanied by aromatization of ring D of anhydroperforine to produce compound 6. The structures of the obtained compounds were established using 1D and 2D NMR spectroscopy and an X-ray crystal structure analysis.