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<p>An attractive approach for the preparation of pyrrolo[2,3-<i>d</i>]pyrimidines has been developed via I<sub>2</sub>/DMSO promoted cascade annulation of 6-amino-1,3-dimethyluracil with aurones. The reaction involves Michael addition, iodination, intramolecular nucleophilic substitution, and spiro ring opening in one-step process, and affords a series of natural product analogues containing pyrrolo[2,3-<i>d</i>]pyrimidine in good yields (up to 99%). Additionally, this protocol exhibits the advantages of high atom economy, inexpensive catalyst, readily available materials, convenient operation and applicability for large-scale synthesis.</p>

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A concise synthesis of pyrrolo[2,3-d]pyrimidine through I2/DMSO promoted cascade annulation

  • 期刊论文

  • 出版模式：

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  • 发表日期：

    2025年8月13日

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  • Meng Xia,
  • Siyuan Jiang,
  • Lingxian Zhao,
  • Ni Deng,
  • Yue Yin,
  • Zhenjie Liu,
  • Suyue Duan,
  • Xianfu Shen,
  • Xuequan Wang

摘要

An attractive approach for the preparation of pyrrolo[2,3-d]pyrimidines has been developed via I2/DMSO promoted cascade annulation of 6-amino-1,3-dimethyluracil with aurones. The reaction involves Michael addition, iodination, intramolecular nucleophilic substitution, and spiro ring opening in one-step process, and affords a series of natural product analogues containing pyrrolo[2,3-d]pyrimidine in good yields (up to 99%). Additionally, this protocol exhibits the advantages of high atom economy, inexpensive catalyst, readily available materials, convenient operation and applicability for large-scale synthesis.