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水中用过一硫酸氢钾复合盐对杂环酮进行绿色氧化反应

Green Oxidation of Heterocyclic Ketones with Oxone in Water.

作者信息

Giraudo Alessandro, Armano Edoardo, Morano Camillo, Pallavicini Marco, Bolchi Cristiano

机构信息

Dipartimento di Scienze Farmaceutiche, Università degli Studi di Milano, via Mangiagalli 25, I-20133, Milano, Italy.

出版信息

J Org Chem. 2023 Nov 3;88(21):15461-15465. doi: 10.1021/acs.joc.3c01513. Epub 2023 Oct 12.

DOI:10.1021/acs.joc.3c01513
PMID:37823876
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC10629238/
Abstract

The recently reported efficient conversion of cyclic ketones to lactones by Oxone in neutral buffered water is extended to heterocyclic ketones, namely, cyclic -Boc azaketones and oxoethers with the aim of obtaining -protected azalactones and their analogues with oxygen in place of nitrogen. -Boc-4-piperidinone and all the cyclic oxoethers were successfully oxidized to lactones, while the azacyclic ketones with nitrogen α-positioned to carbonyl were univocally transformed into -Boc-ω-amino acids and -Boc--formyl-ω-amino acids operating in alkaline water and DMF, respectively.

摘要

最近报道的在中性缓冲水中通过过氧单磺酸钾将环酮高效转化为内酯的方法扩展到了杂环酮，即环 -Boc 氮杂环丁酮和氧杂环醚，目的是获得氮被氧取代的 - 保护氮杂内酯及其类似物。-Boc-4-哌啶酮和所有的环氧杂醚都成功地被氧化为内酯，而羰基α位带有氮的氮杂环酮分别在碱性水和N,N-二甲基甲酰胺中明确地转化为 -Boc-ω-氨基酸和 -Boc-α-甲酰基-ω-氨基酸。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3572/10629238/56e34fbb91e4/jo3c01513_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3572/10629238/3775f66d1678/jo3c01513_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3572/10629238/3f3f53aaafad/jo3c01513_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3572/10629238/e15da683beda/jo3c01513_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3572/10629238/56e34fbb91e4/jo3c01513_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3572/10629238/3775f66d1678/jo3c01513_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3572/10629238/3f3f53aaafad/jo3c01513_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3572/10629238/e15da683beda/jo3c01513_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3572/10629238/56e34fbb91e4/jo3c01513_0004.jpg

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