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<p>Spirocyclic motifs are present in natural products and play an important role in drug discovery. The synthesis of spirocyclic compounds, however, often presents significant challenges. We present a simple and efficient strategy towards the construction of spiro[cyclohexane-1,2'-naphthalene]-2,4-diene scaffolds. The base-mediated dimerisation of substituted 1,2-bis(bromomethyl)benzene derivatives led to spiro compounds in a Diels–Alder reaction via <i>o</i>-quinodimethane intermediates. Two target compounds were obtained and fully structurally characterized by NMR spectroscopy and single crystal X-ray diffraction analysis.</p> Graphical abstract <p></p>

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Synthesis and characterisation of new substituted o-quinodimethane dimers via Diels–Alder reaction: formation of spiro compounds

  • 期刊论文

  • 出版模式：

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  • 发表日期：

    2026年6月23日

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  • Alexander Wolf,
  • Erik Hajdu,
  • Luca Riener,
  • Din Sabic,
  • Uwe Monkowius,
  • Herbert Angleitner

摘要

Spirocyclic motifs are present in natural products and play an important role in drug discovery. The synthesis of spirocyclic compounds, however, often presents significant challenges. We present a simple and efficient strategy towards the construction of spiro[cyclohexane-1,2'-naphthalene]-2,4-diene scaffolds. The base-mediated dimerisation of substituted 1,2-bis(bromomethyl)benzene derivatives led to spiro compounds in a Diels–Alder reaction via o-quinodimethane intermediates. Two target compounds were obtained and fully structurally characterized by NMR spectroscopy and single crystal X-ray diffraction analysis.

Graphical abstract