Suppr超能文献

一锅法将水杨醛转化为螺环氧二烯酮:连续流中的阿德勒-贝克尔反应

One-Pot Transformation of Salicylaldehydes to Spiroepoxydienones the Adler-Becker Reaction in a Continuous Flow.

作者信息

Rosatella Andreia A, Afonso Carlos A M

机构信息

Research Institute for Medicines (iMed.ULisboa), Faculty of Pharmacy, University of Lisbon, Av. Prof. Gama Pinto, 1649-003 Lisbon, Portugal.

CBIOS-Universidade Lusófona's Research Center for Biosciences & Health Technologies, Campo Grande, 376, 1749-024 Lisbon, Portugal.

出版信息

ACS Omega. 2022 Mar 31;7(14):11570-11577. doi: 10.1021/acsomega.1c05559. eCollection 2022 Apr 12.

Abstract

The Adler-Becker reaction is a useful approach for the oxidative dearomatization of salicylic alcohols to spiroepoxydienones and has been applied in the total synthesis of several natural products. Despite the advantages, the substrate and product instability under the reaction conditions can decrease the reaction efficiency, leading to lower yields. Herein, we report the Adler-Becker reaction in a continuous flow for the transformation of reduced salicylaldehydes into spiroepoxydienones in a one-pot approach. For that, a heterogeneous oxidant based on periodate is developed, leading to an efficient continuous flow process, with higher productivity and shorter reaction times, when compared with batch conditions.

摘要

阿德勒-贝克尔反应是将水杨醇氧化脱芳构化转化为螺环氧二烯酮的一种有用方法,已应用于多种天然产物的全合成。尽管有这些优点,但反应条件下底物和产物的不稳定性会降低反应效率,导致产率较低。在此,我们报道了一种连续流阿德勒-贝克尔反应,该反应采用一锅法将还原型水杨醛转化为螺环氧二烯酮。为此,开发了一种基于高碘酸盐的非均相氧化剂,与间歇条件相比,该氧化剂可实现高效的连续流过程,具有更高的生产率和更短的反应时间。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d51e/9017099/256afd06dc3e/ao1c05559_0002.jpg

相似文献

1
One-Pot Transformation of Salicylaldehydes to Spiroepoxydienones the Adler-Becker Reaction in a Continuous Flow.
ACS Omega. 2022 Mar 31;7(14):11570-11577. doi: 10.1021/acsomega.1c05559. eCollection 2022 Apr 12.
3
A One-Pot Approach for Bio-Based Arylamines via a Combined Photooxidative Dearomatization-Rearomatization Strategy.
Chemistry. 2022 Jun 15;28(34):e202200309. doi: 10.1002/chem.202200309. Epub 2022 May 11.
4
Controllable one-pot synthesis for scaffold diversity via visible-light photoredox-catalyzed Giese reaction and further transformation.
Chem Commun (Camb). 2020 Mar 7;56(19):2873-2876. doi: 10.1039/c9cc08781h. Epub 2020 Feb 10.
5
Zn(II)-Catalyzed One-Pot Synthesis of Coumarins from Ynamides and Salicylaldehydes.
Org Lett. 2019 May 3;21(9):3422-3426. doi: 10.1021/acs.orglett.9b01181. Epub 2019 Apr 23.
6
Multicatalytic, asymmetric Michael/Stetter reaction of salicylaldehydes and activated alkynes.
Proc Natl Acad Sci U S A. 2010 Nov 30;107(48):20666-71. doi: 10.1073/pnas.1002830107. Epub 2010 Jul 16.
9
Integrated Batch and Continuous Flow Process for the Synthesis of Goniothalamin.
ACS Omega. 2020 Jul 17;5(29):18472-18483. doi: 10.1021/acsomega.0c02390. eCollection 2020 Jul 28.
10
Transformation of alcohols to esters promoted by hydrogen bonds using oxygen as the oxidant under metal-free conditions.
Sci Adv. 2018 Oct 5;4(10):eaas9319. doi: 10.1126/sciadv.aas9319. eCollection 2018 Oct.

本文引用的文献

1
Creating Diversity from Biomass: A Tandem Bio/Metal-Catalysis towards Chemoselective Synthesis of Densely Substituted Furans.
ChemSusChem. 2019 Oct 21;12(20):4629-4635. doi: 10.1002/cssc.201902051. Epub 2019 Sep 18.
2
Enantioselective Phenolic α-Oxidation Using HO via an Unusual Double Dearomatization Mechanism.
J Am Chem Soc. 2019 Feb 13;141(6):2645-2651. doi: 10.1021/jacs.8b13006. Epub 2019 Jan 30.
3
Supported Catalysts for Continuous Flow Synthesis.
Top Curr Chem (Cham). 2018 Nov 24;376(6):46. doi: 10.1007/s41061-018-0225-0.
4
Valorization of Oleuropein via Tunable Acid-Promoted Methanolysis.
ChemSusChem. 2018 Jul 20;11(14):2300-2305. doi: 10.1002/cssc.201800980. Epub 2018 Jul 4.
6
The Hitchhiker's Guide to Flow Chemistry ∥.
Chem Rev. 2017 Sep 27;117(18):11796-11893. doi: 10.1021/acs.chemrev.7b00183. Epub 2017 Jun 1.
7
Multi-step continuous-flow synthesis.
Chem Soc Rev. 2017 Mar 6;46(5):1250-1271. doi: 10.1039/c6cs00830e.
8
Comparison of silver and molybdenum microfocus X-ray sources for single-crystal structure determination.
J Appl Crystallogr. 2015 Jan 30;48(Pt 1):3-10. doi: 10.1107/S1600576714022985. eCollection 2015 Feb 1.
9
Crystal structure refinement with SHELXL.
Acta Crystallogr C Struct Chem. 2015 Jan;71(Pt 1):3-8. doi: 10.1107/S2053229614024218. Epub 2015 Jan 1.
10
Total synthesis of (-)-4-hydroxyzinowol.
J Org Chem. 2014 Sep 19;79(18):8835-49. doi: 10.1021/jo501666x. Epub 2014 Sep 4.

文献AI研究员

20分钟写一篇综述,助力文献阅读效率提升50倍。

立即体验

用中文搜PubMed

大模型驱动的PubMed中文搜索引擎

马上搜索

文档翻译

学术文献翻译模型,支持多种主流文档格式。

立即体验