1,3,4-Oxadiazoles by Ugi-Tetrazole and Huisgen Reaction

Easy to perform, functional group tolerant, and short syntheses of the privileged scaffold oxadiazole are highly desired. Here, a metal-free protocol for MCR-based synthesis of 2,5-disubstituted 1,3,4-oxadiazoles via a Ugi-tetrazole/Huisgen sequence was developed. Optimization and scope and limitati...

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Bibliographic Details
Published in:Organic letters 2019-09, Vol.21 (18), p.7320-7323
Main Authors: Wang, Qian, Mgimpatsang, Kumchok C, Konstantinidou, Markella, Shishkina, Svitlana V, Dömling, Alexander
Format: Article
Language:English
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Letter
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Summary:Easy to perform, functional group tolerant, and short syntheses of the privileged scaffold oxadiazole are highly desired. Here, a metal-free protocol for MCR-based synthesis of 2,5-disubstituted 1,3,4-oxadiazoles via a Ugi-tetrazole/Huisgen sequence was developed. Optimization and scope and limitations of this short and general sequence are described. The reaction was also successfully performed on a gram scale.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b02614