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有机催化的α,β-不饱和酮与异亚丙基丙二腈的[4 + 2]环加成反应：合成螺[3-芳基环己酮]氧化吲哚衍生物

Organocatalyzed [4 + 2] cycloaddition of α,β-unsaturated ketones and isatylidene malononitrile: accessing spiro[3-arylcyclohexanone]oxindole derivatives.

作者信息

Patil Baliram R, Nichinde Chandrakant B, Chaudhari Suryakant S, Krishna Gamidi Rama, Kinage Anil K

机构信息

Chemical Engineering and Process Development Division, Council of Scientific and Industrial Research-National Chemical Laboratory (CSIR-NCL) Pune 411008 India

Academy of Scientific and Innovative Research (AcSIR) Ghaziabad 201002 India.

出版信息

RSC Adv. 2024 Jan 17;14(5):2873-2877. doi: 10.1039/d3ra07652k.

DOI:10.1039/d3ra07652k
PMID:38239455
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC10793649/
Abstract

Herein, we developed a series of compounds featuring spiro[3-arylcyclohexanone]oxindoles through Barbas [4 + 2] cycloaddition reactions between isatylidene malononitrile and α,β-unsaturated ketones using l-proline as an organocatalyst. The reported methodology offers many advantages such as mild reaction conditions, diverse substrate scope with high yields, easy reaction setup, and use of easily synthesizable starting materials.

摘要

在此，我们通过使用L-脯氨酸作为有机催化剂，使异亚丙基丙二腈与α,β-不饱和酮之间发生Barbas [4 + 2]环加成反应，开发了一系列具有螺[3-芳基环己酮]氧化吲哚结构的化合物。所报道的方法具有许多优点，如反应条件温和、底物范围多样且产率高、反应设置简便以及使用易于合成的起始原料。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8cf9/10793649/a2cee3bb8bbe/d3ra07652k-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8cf9/10793649/e54f7d91a845/d3ra07652k-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8cf9/10793649/b62e7357d0dd/d3ra07652k-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8cf9/10793649/f469e67aa7f0/d3ra07652k-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8cf9/10793649/a2cee3bb8bbe/d3ra07652k-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8cf9/10793649/e54f7d91a845/d3ra07652k-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8cf9/10793649/b62e7357d0dd/d3ra07652k-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8cf9/10793649/f469e67aa7f0/d3ra07652k-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8cf9/10793649/a2cee3bb8bbe/d3ra07652k-f3.jpg

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本文引用的文献

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RSC Adv. 2023 Apr 28;13(19):13206-13212. doi: 10.1039/d3ra00510k. eCollection 2023 Apr 24.
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