Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 363, Issue 14, Pages 3607-3614Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.202100249
Keywords
metal-free; oxidative condensation; benzoxazole; catechol; aldehyde
Categories
Funding
- NSF of China [21878072, 21706058, 21573065]
- Natural Science Foundation of Hunan Province [2020JJ2011]
- China Postdoctoral Science Foundation [2019M662774]
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A simple and green method for the synthesis of benzoxazoles from catechols, aldehydes, and ammonium acetate using NaIO4 as an oxidant under metal- and additive-free conditions has been developed. The protocol results in high yields of benzoxazoles with excellent functional group tolerance, with mechanistic investigations revealing the involvement of a unique intermediate.
Benzoxazoles extensively exist in biologically active compounds, natural products, pharmaceuticals and functional materials. Thus, facile and green synthesis of such valuable compounds from easily available substrates will make a contribution to drug, material, and fine chemistry. A method for the synthesis of benzoxazoles from catechols, aldehydes and ammonium acetate is developed using NaIO4 as oxidant under metal- and additive-free conditions. A broad range of benzoxazoles including some fluorescent whitening agents, JTP-426467 and tafamidis analogues are synthesized in 56-95% yields with outstanding functional group tolerance. Mechanistic investigations suggest that an interesting o-iminocyclohexa-diene alcohol intermediate is involved in the reaction. These salient features of the protocol make it an alternative for the synthesis of benzoxazoles.
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