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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

Synlett(2022)

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Abstract
A facile approach for the synthesis of benzimidazolones via a Ph3P–I2 promoted reaction of hydroxamic acids is reported. 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. The method allows the direct preparation of a single regioisomer of N-monosubstituted derivatives using readily accessible starting materials and low-cost reagents with broad substrate scope.
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Key words
benzimidazol-2-ones,hydroxamic acids,triphenylphosphine,iodine,Lossen rearrangement
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