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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

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