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2-芳基-1-四氢萘酮中碳-碳键的酸催化空气氧化断裂

Acid-Catalyzed Air-Oxidative Fragmentation of the Carbon-Carbon Bond in 2-Aryl-1-tetralones.

作者信息

Ghosh Partha

机构信息

Department of Chemistry, Central University of Jharkhand, Brambe, Ranchi 835205, India.

出版信息

ACS Omega. 2019 May 2;4(5):8065-8070. doi: 10.1021/acsomega.9b00732. eCollection 2019 May 31.

DOI:10.1021/acsomega.9b00732
PMID:31459896
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6648412/
Abstract

Catalytic auto-oxidation with air is a highly desirable method for green synthesis. Described here is a method for acid-catalyzed one step air-oxidative fragmentation of 2-aryl-1-tetralones to alkyl-2-(3-oxo-3-aryl) benzoates in the presence of alcohol. This method was then demonstrated using concise synthesis of a key intermediate of antiasthma drug Montelukast sodium. Moreover, the paradoxical nature of the reaction in which ester forms but only within a low concentration threshold of alcohol helps in understanding the mechanism of the reaction.

摘要

用空气进行催化自动氧化是绿色合成中非常理想的方法。本文描述了一种在醇存在下将2-芳基-1-四氢萘酮酸催化一步空气氧化裂解为2-(3-氧代-3-芳基)苯甲酸烷基酯的方法。然后通过简明合成抗哮喘药物孟鲁司特钠的关键中间体来证明该方法。此外，该反应的矛盾性质，即酯仅在低浓度醇阈值内形成，有助于理解反应机理。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c799/6648412/a3f13a17d955/ao-2019-00732f_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c799/6648412/083002935da7/ao-2019-00732f_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c799/6648412/0e9d8a446594/ao-2019-00732f_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c799/6648412/a3f13a17d955/ao-2019-00732f_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c799/6648412/083002935da7/ao-2019-00732f_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c799/6648412/0e9d8a446594/ao-2019-00732f_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c799/6648412/a3f13a17d955/ao-2019-00732f_0003.jpg

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本文引用的文献

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N-heterocyclic carbene-palladium(II)-1-methylimidazole complex catalyzed α-arylation reactions of tetralones with aryl chlorides and further transformation of the products.
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