4.6 Article

Copper(ii)-catalyzed oxidative ipso-annulation of N-arylpropiolamides and biaryl ynones with 1,3-diketones: construction of diketoalkyl spiro-trienones

Journal

ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 20, Issue 34, Pages 6879-6889

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/d2ob01282k

Keywords

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Funding

  1. Science and Engineering Research Board (SERB), Department of Science and Technology, New Delhi [CRG/2021/007367, IICT/Pubs./2022/152]
  2. University Grants Commission (UGC)
  3. Department of Science and Technology (DST-INSPIRE) [IF180803]

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A copper-catalyzed ipso-annulation reaction of N-(p-methoxyaryl)propiolamides with 1,3-diketones has been developed, enabling the synthesis of diketoalkylated spiro[4.5]trienones and spiro[5.5]trienones.
An unprecedented copper-catalyzed ipso-annulation reaction of N-(p-methoxyaryl)propiolamides with 1,3-diketones has been developed, which enables the assembly of diketoalkylated spiro[4.5]trienones involving oxidative dearomatization in the presence of ammonium persulfate [(NH4)(2)S2O8] as the oxidant. This protocol was extended to biaryl ynones, efficiently affording the diketoalkylated spiro[5.5]trienones in good yields. The significance of the diketoalkyl functionality has been illustrated by further transformation into 3-pyrazoyl spiro-trienone, a structurally unique motif.

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