PIFA 介导的苯酚系 1,2-二唑分子内脱芳作用:螺环己二烯酮吡唑并[3,4-b]哌啶酮的合成

Synthesis Pub Date : 2024-08-08 DOI:10.1055/a-2382-9631
Pradeep Natarajan, Pratibha Bachhley, Sweta Tripathy, Ashok Vasantharaj P, S. Peruncheralathan
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引用次数: 0

摘要

近年来,由于螺环基团具有与生物靶标结合的独特能力,其在药物发现中的重要性与日俱增。我们首次展示了 PIFA 介导的苯酚系吡唑的脱芳香螺环化,突出了吡唑分子的分子内捕获。这种方法能有效地得到各种螺环己二烯酮吡唑并[3,4-b]哌啶酮,收率高达 82%。机理研究表明,脱芳烃过程涉及阳离子中间体。
本文章由计算机程序翻译,如有差异,请以英文原文为准。

PIFA-Mediated Intramolecular Dearomatization of Phenol-Tethered 1,2-Diazoles: Synthesis of Spirocyclohexadienone Pyrazolo[3,4-b]piperidinones

PIFA-Mediated Intramolecular Dearomatization of Phenol-Tethered 1,2-Diazoles: Synthesis of Spirocyclohexadienone Pyrazolo[3,4-b]piperidinones
In recent years, the significance of spirocyclic motifs in drug discovery has increased, owing to their unique ability to engage biological targets. We present the first example of PIFA-mediated dearomative spirocyclization of phenol-tethered pyrazoles, highlighting intramolecular trapping by the pyrazole moiety. This method efficiently affords a variety of spirocyclohexadienone pyrazolo[3,4-b]piperidinones with yields of up to 82%. Mechanistic studies reveal that the dearomatization process involves a cationic intermediate.
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