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基于天然产物导向的光诱导 1-烯基苯并三唑的去氮环化反应。

Natural Product-Oriented Photo-Induced Denitrogenative Annulations of 1-Alkenylbenzotriazoles.

机构信息

School of Pharmaceutical Sciences, MOE Key Laboratory of Bioorganic Phosphorus Chemistry & Chemical Biology, Tsinghua University, Beijing 100084, China.

College of Chemical Engineering, Qinghai University, Xining 810016, China.

出版信息

Molecules. 2023 Jan 2;28(1):363. doi: 10.3390/molecules28010363.

DOI:10.3390/molecules28010363
PMID:36615557
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9823906/
Abstract

The photo-induced denitrogenative annulations of a variety of 1-alkenylbenzotriazoles were investigated. By judiciously manipulating the structural variations of 1-alkenylbenzotriazoles, two characteristic polycyclic skeletons associated with monoterpene indole alkaloids were constructed through a diverted and controllable manner. The present work not only enriches the photochemistry of 1-alkenylbenzotriazoles, but also offers a unified approach to access skeletally diverse indole alkaloid scaffolds.

摘要

研究了多种 1-烯基苯并三唑的光致脱氮环化反应。通过巧妙地控制 1-烯基苯并三唑的结构变化,以一种定向和可控的方式构建了两种与单萜吲哚生物碱相关的特征多环骨架。本工作不仅丰富了 1-烯基苯并三唑的光化学,而且为获得骨架多样的吲哚生物碱支架提供了一种统一的方法。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f548/9823906/70cdc39fc3d8/molecules-28-00363-sch005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f548/9823906/848e52200446/molecules-28-00363-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f548/9823906/1d1b8a6f5e6f/molecules-28-00363-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f548/9823906/37d5931fbaaf/molecules-28-00363-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f548/9823906/85ab9167adfb/molecules-28-00363-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f548/9823906/cf210c414528/molecules-28-00363-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f548/9823906/70cdc39fc3d8/molecules-28-00363-sch005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f548/9823906/848e52200446/molecules-28-00363-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f548/9823906/1d1b8a6f5e6f/molecules-28-00363-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f548/9823906/37d5931fbaaf/molecules-28-00363-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f548/9823906/85ab9167adfb/molecules-28-00363-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f548/9823906/cf210c414528/molecules-28-00363-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f548/9823906/70cdc39fc3d8/molecules-28-00363-sch005.jpg

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本文引用的文献

1
1,2,3-Triazole and Its Analogues: New Surrogates for Diazo Compounds.1,2,3-三唑及其类似物:重氮化合物的新型替代品。
Chem Rev. 2022 Aug 10;122(15):13108-13205. doi: 10.1021/acs.chemrev.1c00991. Epub 2022 Jul 19.
2
Palladium-Catalyzed Asymmetric Tandem Denitrogenative Heck/Tsuji-Trost of Benzotriazoles with 1,3-Dienes.钯催化的苯并三唑与 1,3-二烯的不对称串联 denitrogenative Heck/Tsuji-Trost 反应。
J Am Chem Soc. 2021 Aug 25;143(33):13010-13015. doi: 10.1021/jacs.1c07212. Epub 2021 Aug 17.
3
Total Synthesis of (+)-Alsmaphorazine C and Formal Synthesis of (+)-Strictamine: A Photo-Fries Approach.
(+)-Alsmaphorazine C 的全合成和(+)-Strictamine 的形式合成:光-Fries 方法。
Angew Chem Int Ed Engl. 2021 May 3;60(19):10603-10607. doi: 10.1002/anie.202101752. Epub 2021 Apr 6.
4
Chemical Diversity and Bioactivities of Monoterpene Indole Alkaloids (MIAs) from Six Apocynaceae Genera.六种夹竹桃科植物中单萜吲哚生物碱(MIAs)的化学多样性和生物活性。
Molecules. 2021 Jan 18;26(2):488. doi: 10.3390/molecules26020488.
5
Synthesis of Heterocycles through Denitrogenative Cyclization of Triazoles and Benzotriazoles.通过三唑和苯并三唑的脱氮环化合成杂环化合物。
Chemistry. 2020 Sep 16;26(52):11931-11945. doi: 10.1002/chem.202000674. Epub 2020 Jul 8.
6
Indole alkaloids: 2012 until now, highlighting the new chemical structures and biological activities.吲哚生物碱:2012 年至今,重点介绍新的化学结构和生物活性。
Fitoterapia. 2020 Jun;143:104558. doi: 10.1016/j.fitote.2020.104558. Epub 2020 Mar 17.
7
Renaissance of Ring-Opening Chemistry of Benzotriazoles: New Wine in an Old Bottle.苯并三唑开环反应的复兴:旧瓶中的新酒。
Chem Rec. 2020 Jul;20(7):693-709. doi: 10.1002/tcr.201900088. Epub 2020 Jan 9.
8
Palladium/Copper-Catalyzed Denitrogenative Alkylidenation and -Alkynylation Reaction of 1,2,3-Benzotriazin-4(3)-ones.钯/铜催化的1,2,3-苯并三嗪-4(3)-酮的脱氮亚烷基化和脱氮炔基化反应
Org Lett. 2020 Jan 17;22(2):542-546. doi: 10.1021/acs.orglett.9b04297. Epub 2019 Dec 30.
9
Cu-Catalyzed Arylation/Acyl Migration Cascade Reaction of Enaminones: Access to N-Fused Polycyclic and 2,3-Disubstituted Indoles.铜催化的烯胺酮的芳基化/酰基迁移级联反应:N-稠合多环和 2,3-二取代吲哚的合成。
J Org Chem. 2019 Jun 21;84(12):7995-8005. doi: 10.1021/acs.joc.9b00866. Epub 2019 Jun 10.
10
Synthesis of N-Fused Polycyclic Indoles via Ligand-Free Palladium-Catalyzed Annulation/Acyl Migration Reaction.无配体促进的钯催化稠环吲哚的环化/酰基迁移反应合成
Org Lett. 2019 Feb 15;21(4):1082-1086. doi: 10.1021/acs.orglett.8b04128. Epub 2019 Jan 29.