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靛蓝与烯丙基反应物的串联反应。

Cascade Reactions of Indigo with an Allenylic Reactant.

作者信息

Rahayu Dyah U C, Richardson Christopher, Bremner John B, Keller Paul A

机构信息

School of Science, Molecular Horizons, University of Wollongong, Wollongong, NSW 2522, Australia.

出版信息

Molecules. 2025 Jul 8;30(14):2899. doi: 10.3390/molecules30142899.

DOI:10.3390/molecules30142899
PMID:40733166
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC12299176/
Abstract

The base-enabled reaction of buta-2,3-dien-1-yl methanesulfonate with the readily available and cheap dye indigo resulted in the convenient one-pot synthesis of benzoindolonaphthyridinedione and benzoazepinopyridoindolediones, with the latter representing two novel heterocyclic scaffolds. Despite the low yields, the allenylic alkylation of indigo significantly contributes to the new chemistry of this compound, providing new mechanistic insights and reactivity boundaries.

摘要

丁-2,3-二烯-1-基甲磺酸酯与易于获得且价格低廉的染料靛蓝在碱作用下发生反应,可方便地一锅法合成苯并吲哚并萘啶二酮和苯并氮杂卓吡啶并吲哚二酮,后者代表两种新型杂环骨架。尽管产率较低,但靛蓝的烯丙基烷基化对该化合物的新化学性质有显著贡献,提供了新的机理见解和反应活性边界。

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本文引用的文献

1
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Molecules. 2024 Sep 6;29(17):4242. doi: 10.3390/molecules29174242.
2
Palladium-catalyzed asymmetric [4 + 3] cycloaddition of methylene-trimethylenemethane: access to seven-membered exocyclic axially chiral allenes.钯催化的亚甲基-三亚甲基甲烷的不对称[4 + 3]环加成反应:合成七元外环轴向手性联烯
Chem Sci. 2024 May 17;15(25):9703-9708. doi: 10.1039/d4sc01649a. eCollection 2024 Jun 26.
3
Photochromic derivatives of indigo: historical overview of development, challenges and applications.
靛蓝的光致变色衍生物:发展的历史概述、挑战与应用
Beilstein J Org Chem. 2024 Feb 7;20:228-242. doi: 10.3762/bjoc.20.23. eCollection 2024.
4
A Blueprint for Transforming Indigos to Photoresponsive Molecular Tools.将靛蓝转变为光响应分子工具的蓝图。
Chemistry. 2023 Aug 1;29(43):e202300981. doi: 10.1002/chem.202300981. Epub 2023 May 22.
5
Direct Catalytic Asymmetric and Regiodivergent N1- and C3-Allenylic Alkylation of Indoles.吲哚的直接催化不对称和区域发散 N1-和 C3-烯丙基烷基化反应。
Angew Chem Int Ed Engl. 2023 May 15;62(21):e202300844. doi: 10.1002/anie.202300844. Epub 2023 Apr 13.
6
Unveiling the Chemistry and Synthetic Potential of Catalytic Cycloaddition Reaction of Allenes: A Review.揭开烯丙基催化环加成反应的化学与合成潜力:综述。
Molecules. 2023 Jan 10;28(2):704. doi: 10.3390/molecules28020704.
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J Org Chem. 2021 Dec 17;86(24):17620-17628. doi: 10.1021/acs.joc.1c01726. Epub 2021 Nov 24.
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J Org Chem. 2020 Dec 4;85(23):15743-15751. doi: 10.1021/acs.joc.0c02403. Epub 2020 Nov 23.