Direct Synthesis of N-Monosubstituted Benzimidazol-2-ones via Ph3P-I2-Mediated Reaction of Hydroxamic Acids
Nittaya Wiriya, Dolnapa Yamano, Surat Hongsibsong, Mookda Pattarawarapan, Wong Phakhodee*
*Department of Chemistry, Faculty of Science, Chiang Mai
University, Chiang Mai, 50200, Thailand,
Email: wongp2577
gmail.com
N. Wiriya, D. Yamano, S. Hongsibsong, M. Pattarawarapan, W. Phakhodee, Synlett, 2022, 33, 1468-1472.
DOI: 10.1055/s-0040-1719897
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Abstract
The combination of Ph3P and I2 promotes a synthesis of benzimidazolones from readily accessible hydroxamic acids. Upon Lossen-type rearrangement of the O-activated hydroxamic acids, the in situ generated isocyanates undergo an intramolecular attack by ortho N-nucleophiles producing the cyclized products in good yields under mild conditions.
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Key Words
benzimidazol-2-ones, hydroxamic acids, triphenylphosphine, iodine, Lossen rearrangement
ID: J72-Y2022
