Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 20, Issue 34, Pages 6879-6889Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d2ob01282k
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Funding
- Science and Engineering Research Board (SERB), Department of Science and Technology, New Delhi [CRG/2021/007367, IICT/Pubs./2022/152]
- University Grants Commission (UGC)
- 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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