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恶(硫)二唑芳基硫醚的生物催化合成。

Biocatalytic synthesis of oxa(thia)diazole aryl thioethers.

作者信息

Mottaghi Amlashi Donya, Mobini Sepideh, Shahedi Mansour, Habibi Zohreh, Bavandi Hossein, Yousefi Maryam

机构信息

Department of Organic Chemistry, Shahid Beheshti University, Daneshjou Boulevard, Tehran, 1983969411, Iran.

Avicenna Research Institute, Nanobiotechnology Research Center, ACECR, Tehran, Iran.

出版信息

Sci Rep. 2024 Aug 22;14(1):19468. doi: 10.1038/s41598-024-70239-3.

DOI:10.1038/s41598-024-70239-3
PMID:39174618
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11341560/
Abstract

A novel approach for the synthesis of 1,3,4-oxa(thia)diazole aryl thioethers through a biocatalytic strategy has been introduced. By leveraging Myceliophthora thermophila laccase (Novozym 51003) as a catalyst, catechol undergoes oxidation to ortho-quinone, facilitating subsequent 1,4-thia-Michael addition reactions. The method offers efficiency and mild reaction conditions, demonstrating promise for sustainable synthesis pathways in organic chemistry. Using this approach, 13 new derivatives of 2,5-disubstituted-1,3,4-oxa(thia)diazole aryl thioethers, with a yield of 46-94%, were synthesized.

摘要

介绍了一种通过生物催化策略合成1,3,4-氧杂(硫杂)二唑芳基硫醚的新方法。利用嗜热毁丝霉漆酶(诺维信51003)作为催化剂,邻苯二酚被氧化为邻醌,促进随后的1,4-硫杂-迈克尔加成反应。该方法具有高效性和温和的反应条件,为有机化学中的可持续合成途径展示了前景。采用这种方法,合成了13种2,5-二取代-1,3,4-氧杂(硫杂)二唑芳基硫醚的新衍生物,产率为46-94%。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/795b/11341560/8ca564ce3385/41598_2024_70239_Fig4_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/795b/11341560/abf19b37b48c/41598_2024_70239_Fig1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/795b/11341560/c72202a479ee/41598_2024_70239_Fig2_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/795b/11341560/1ab83666f720/41598_2024_70239_Fig3_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/795b/11341560/8ca564ce3385/41598_2024_70239_Fig4_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/795b/11341560/abf19b37b48c/41598_2024_70239_Fig1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/795b/11341560/c72202a479ee/41598_2024_70239_Fig2_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/795b/11341560/1ab83666f720/41598_2024_70239_Fig3_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/795b/11341560/8ca564ce3385/41598_2024_70239_Fig4_HTML.jpg

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