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由N-酰基腙电合成1,3,4-恶二唑

An Electrosynthesis of 1,3,4-Oxadiazoles from N-Acyl Hydrazones.

作者信息

Chen Luke, Thompson James D F, Jamieson Craig

机构信息

Medicinal Chemistry, GSK, Gunnels Wood Road, Stevenage, SG1 2NY, United Kingdom.

Pure & Applied Chemistry, University of Strathclyde, Glasgow, G1 1XL, United Kingdom.

出版信息

Chemistry. 2024 Dec 10;30(69):e202403128. doi: 10.1002/chem.202403128. Epub 2024 Oct 30.

DOI:10.1002/chem.202403128
PMID:39291449
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11632415/
Abstract

The 1,3,4-oxadiazole is a widely encountered motif in the areas of pharmaceuticals, materials, and agrochemicals. This work has established a mediated electrochemical synthesis of 2,5-disubstituted 1,3,4-oxadiazoles from N-acyl hydrazones. Using DABCO as the optimal redox mediator has enabled a mild oxidative cyclisation, without recourse to stoichiometric oxidants. In contrast to previous methods, this indirect electrochemical oxidation has enabled a broad range of substrates to be accessed, with yields of up to 83 %, and on gram scale. The simplicity of the method has been further demonstrated by the development of a one-pot procedure, directly transforming readily available aldehydes and hydrazides into valuable heterocycles.

摘要

1,3,4-恶二唑是在药物、材料和农用化学品领域广泛存在的结构单元。这项工作建立了一种由N-酰基腙介导的电化学合成2,5-二取代1,3,4-恶二唑的方法。使用1,4-二氮杂二环[2.2.2]辛烷（DABCO）作为最佳氧化还原介质能够实现温和的氧化环化反应，无需使用化学计量的氧化剂。与之前的方法相比，这种间接电化学氧化能够合成多种底物，产率高达83%，且可达到克级规模。通过开发一锅法程序，将容易获得的醛和酰肼直接转化为有价值的杂环化合物，进一步证明了该方法的简便性。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ce7/11632415/078f133dcf1f/CHEM-30-e202403128-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ce7/11632415/5dd216dc020a/CHEM-30-e202403128-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ce7/11632415/74f9083225b2/CHEM-30-e202403128-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ce7/11632415/4e1e087d9bb5/CHEM-30-e202403128-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ce7/11632415/f46c1c4cc5c4/CHEM-30-e202403128-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ce7/11632415/ef6d71e9d65f/CHEM-30-e202403128-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ce7/11632415/61b32cd6c24a/CHEM-30-e202403128-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ce7/11632415/078f133dcf1f/CHEM-30-e202403128-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ce7/11632415/5dd216dc020a/CHEM-30-e202403128-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ce7/11632415/74f9083225b2/CHEM-30-e202403128-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ce7/11632415/4e1e087d9bb5/CHEM-30-e202403128-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ce7/11632415/f46c1c4cc5c4/CHEM-30-e202403128-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ce7/11632415/ef6d71e9d65f/CHEM-30-e202403128-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ce7/11632415/61b32cd6c24a/CHEM-30-e202403128-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ce7/11632415/078f133dcf1f/CHEM-30-e202403128-g006.jpg

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Therapeutic potential of 1,3,4-oxadiazoles as potential lead compounds for the treatment of Alzheimer's disease.1,3,4-恶二唑作为治疗阿尔茨海默病潜在先导化合物的治疗潜力
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