Direct Synthesis of N-Monosubstituted Benzimidazol-2-ones via Ph3 P–I2 -Mediated Reaction of Hydroxamic Acids.

Autor: Wiriya, Nittaya, Yamano, Dolnapa, Hongsibsong, Surat, Pattarawarapan, Mookda, Phakhodee, Wong
Předmět:
Zdroj: Synlett; Sep2022, Vol. 33 Issue 14, p1468-1472, 5p
Abstrakt: A facile approach for the synthesis of benzimidazolones via a Ph3 P–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. [ABSTRACT FROM AUTHOR]
Databáze: Complementary Index