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

Biocatalytic synthesis of oxa(thia)diazole aryl thioethers

Donya Mottaghi Amlashi  1 , Sepideh Mobini  1 , Mansour Shahedi  1 , Zohreh Habibi  2 , Hossein Bavandi  1 , Maryam Yousefi  3
Affiliations

Biocatalytic synthesis of oxa(thia)diazole aryl thioethers

Donya Mottaghi Amlashi et al. Sci Rep. .

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.

Keywords: Aryl thioether; Biocatalyst; Enzyme; Laccase; Oxa(thia)diazole.

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Conflict of interest statement

The authors declare no competing interests.

Figures

Figure 1
Figure 1
Structures of some biologically active compounds containing 1,3,4-oxa(thia)diazole thioether scaffolds.
Figure 2
Figure 2
Previous works and this work.
Figure 3
Figure 3
The gram scale reaction for compound 3a.
Figure 4
Figure 4
Proposed mechanism.
See this image and copyright information in PMC

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