Diastereoselective [3 + 2] Cycloaddition of Quinoxalin-2(1H)-ones with Donor–Acceptor Cyclopropanes: Efficient Synthesis of Tetrahydro pyrrolo[1,2-a]quinoxalin-4(5H)-ones,The Journal of Organic Chemistry

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Diastereoselective [3 + 2] Cycloaddition of Quinoxalin-2(1H)-ones with Donor–Acceptor Cyclopropanes: Efficient Synthesis of Tetrahydro pyrrolo[1,2-a]quinoxalin-4(5H)-ones
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2021-11-15 , DOI: 10.1021/acs.joc.1c01872
Himangsu Sekhar Dutta ₁ , Ashfaq Ahmad ₂ , Afsar Ali Khan ₁ , Mohit Kumar ₁ , Raziullah ₂ , Jayanti Vaishnav ₃ , Manoj Gangwar ₄ , Ravi Sankar Ampapathi ₃ , Dipankar Koley _{1,

2}

Affiliation

A ytterbium triflate-catalyzed diastereoselective [3 + 2] cycloaddition of quinoxalinones with donor–acceptor cyclopropanes and cyclobutanes is described. A series of tetrahydropyrrolo-quinoxalinone derivatives were obtained in high yields (up to 96%) with excellent diastereoselectivities (up to 46:1). Other medicinally important heterocycles like benzoxazinone, isoquinoxalinone, and dibenzoxazepine derivatives were also suitable for the desired annulation reaction. The current method is applicable for the scale-up reaction. Further, the utility of this annulation reaction is demonstrated by the synthesis of densely functionalized proline derivatives.

中文翻译：

Quinoxalin-2(1H)-ones 与供体-受体环丙烷的非对映选择性 [3 + 2] 环加成：四氢吡咯并[1,2-a]quinoxalin-4(5H)-ones 的高效合成

描述了三氟甲磺酸镱催化的喹喔啉酮与供体-受体环丙烷和环丁烷的非对映选择性 [3 + 2] 环加成反应。以高产率（高达 96%）获得一系列四氢吡咯并喹喔啉酮衍生物，并具有优异的非对映选择性（高达 46:1）。其他药用上重要的杂环化合物，如苯并恶嗪酮、异喹喔啉酮和二苯并恶唑衍生物，也适用于所需的环化反应。本方法适用于放大反应。此外，这种环化反应的效用通过密集官能化脯氨酸衍生物的合成得到证实。

更新日期：2021-12-03

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