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DOI: 10.1055/a-2689-2278
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PIFA-Mediated Ring-Opening/Coupling Reaction of Benzoxazoles: Access to 2-Hydroxy Diarylureas

Xizhong Song
1   State Key Laboratory of Southwestern Chinese Medicine Resources, School of Pharmacy, Chengdu University of Traditional Chinese Medicine, Chengdu, China (Ringgold ID: RIN118385)
2   Technical Development Department, Jiangxi Fangzhu Pharmaceutical CO Ltd, Xinyu Xinyu, China
,
Wei Yin
2   Technical Development Department, Jiangxi Fangzhu Pharmaceutical CO Ltd, Xinyu Xinyu, China
,
Xiaowen Zeng
2   Technical Development Department, Jiangxi Fangzhu Pharmaceutical CO Ltd, Xinyu Xinyu, China
,
Wenping Zhang
2   Technical Development Department, Jiangxi Fangzhu Pharmaceutical CO Ltd, Xinyu Xinyu, China
,
Wenyan Fu
3   School of Pharmacy, The Second Affiliated Hospital of Nanchang University, Nanchang, China
,
Limei Qian
2   Technical Development Department, Jiangxi Fangzhu Pharmaceutical CO Ltd, Xinyu Xinyu, China
,
Yi Jin
2   Technical Development Department, Jiangxi Fangzhu Pharmaceutical CO Ltd, Xinyu Xinyu, China
,
Ming Yang
1   State Key Laboratory of Southwestern Chinese Medicine Resources, School of Pharmacy, Chengdu University of Traditional Chinese Medicine, Chengdu, China (Ringgold ID: RIN118385)
› Institutsangaben
Gefördert durch: JiangXi Province Leading Talent Project of Innovation of Double Thousand Plan S2021DQKJ2195
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A efficient method for synthesizing asymmetric 2-hydroxy diaryl ureas has been developed via phenyliodine bis(trifluoroacetate) (PIFA)-mediated ring-opening/coupling of benzoxazoles with aryl isocyanates or isothiocyanates. This transition-metal-free protocol operates under mild conditions and utilizes Al2O3/H+ as a key additive, achieving high yields (up to 95%) with broad substrate scope. The reaction proceeds through a proposed PIFA-induced ring-opening of benzoxazole followed by nucleophilic addition, providing direct access to pharmacologically and materially valuable 2-hydroxy diaryl ureas while avoiding toxic reagents and high-pressure equipment. This strategy addresses limitations of traditional urea syntheses, offering operational simplicity and scalability.



Publikationsverlauf

Eingereicht: 19. Juni 2025

Angenommen nach Revision: 14. August 2025

Accepted Manuscript online:
24. August 2025

© . The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution License, permitting unrestricted use, distribution, and reproduction so long as the original work is properly cited. (https://creativecommons.org/licenses/by/4.0/).

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