钯催化级联快速获得四氢- 4H -吡唑[3,4 - d]吡咯[1,2 - a]嘧啶- 4 - 1四环融合杂环

IF 2.8 4区化学 Q1 CHEMISTRY, ORGANIC

Asian Journal of Organic Chemistry Pub Date : 2025-05-01 DOI:10.1002/ajoc.202500012

Navin Pandit , Youyoung Kim , Jimin Heo , Seojin Jang , Kyu Myung Lee , Kwan‐Young Jung

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引用次数: 0

摘要

级联反应是一种很有吸引力的合成杂环的方法。我们报道了基于Suzuki偶联级联序列构建(6R) - 6 -羟基- 1,3a,6,11a -四氢- 4H -吡唑[3 ',4 ':4,5]嘧啶[2,1 - a]异吲哚- 4 - 1 - 1融合杂环和碱基介导的分子内环化形成C - N键的第一种合成方法。该方案具有很高的立体特异性，因为分子内环化在产物中产生一个具有独家R构型的手性中心。基于密度泛函理论计算，提出了级联反应的机理。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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Palladium‐Catalyzed Cascade for Rapid Access to Tetrahydro‐4H‐pyrazolo[3,4‐d]pyrrolo[1,2‐a]pyrimidin‐4‐one Tetracyclic Fused Heterocycles

The cascade reaction is an attractive strategy for building fused heterocycles. We report the first synthetic methodology to construct (6R)‐6‐hydroxy‐1,3a,6,11a‐tetrahydro‐4H‐pyrazolo[3′,4′:4,5]pyrimido[2,1‐a]isoindol‐4‐one fused heterocycles based on a cascade sequence of Suzuki coupling to form a C−C bond and base‐mediated intramolecular cyclization to form a C−N bond. This protocol exhibits high stereospecificity, as intramolecular cyclization generates a chiral center with exclusive R‐configuration in the product. A mechanism for the cascade reaction is proposed based on density functional theory calculations.

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来源期刊

Asian Journal of Organic Chemistry CHEMISTRY, ORGANIC-

CiteScore

4.70

自引率

3.70%

发文量

372

期刊介绍： Organic chemistry is the fundamental science that stands at the heart of chemistry, biology, and materials science. Research in these areas is vigorous and truly international, with three major regions making almost equal contributions: America, Europe and Asia. Asia now has its own top international organic chemistry journal—the Asian Journal of Organic Chemistry (AsianJOC) The AsianJOC is designed to be a top-ranked international research journal and publishes primary research as well as critical secondary information from authors across the world. The journal covers organic chemistry in its entirety. Authors and readers come from academia, the chemical industry, and government laboratories.