Gold-Catalyzed [4 + 1] Heterocyclization of Hydroxamic Acid and Nonactivated Alkyne: A Protocol to Construct 5‑Methyl-1,4,2-dioxazole

A novel gold-catalyzed [4 + 1] heterocyclization of nonactivated alkyne and hydroxamic acid is developed for the regiospecific synthesis of 5-methyl-1,4,2-dioxazole, which is an important structural motif in various bioactive molecules. The current methodology is characterized by high efficiency, si...

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Bibliographic Details
Published in:Journal of organic chemistry 2023-01, Vol.88 (1), p.433-441
Main Authors: He, Xiao-Lin, Ma, Xin-Ran, Yan, Nan, Zhang, Xiao-Wei
Format: Article
Language:English
Subjects:
Alkynes - chemistry
Catalysis
Cyclization
Gold - chemistry
Hydroxamic Acids - chemistry
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Summary:A novel gold-catalyzed [4 + 1] heterocyclization of nonactivated alkyne and hydroxamic acid is developed for the regiospecific synthesis of 5-methyl-1,4,2-dioxazole, which is an important structural motif in various bioactive molecules. The current methodology is characterized by high efficiency, simple operation, mild reaction conditions, and good functional group compatibility. Moreover, gram-scale synthesis and synthetic application toward bioactive molecular skeletons have been realized.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.2c02427