1033079-57-0Relevant academic research and scientific papers
Cu-Catalyzed Synthesis of Benzoxazole with Phenol and Cyclic Oxime
Wang, Zheng-Hai,Wang, Dong-Hui
supporting information, p. 782 - 785 (2022/01/20)
A Cu-catalyzed straightforward synthesis of benzoxazoles from free phenols and cyclic oxime esters is reported. The mild reaction conditions tolerate various electron-withdrawing and electron-donating functional groups on both substrates, affording benzoxazoles in moderate to good yields. With this protocol, large-scale syntheses of Ezutromid and Flunoxaprofe in one or two steps are demonstrated. A catalytic mechanism, which includes Cu-catalyzed amination via inner-sphere electron transfer and consequent annulation, is proposed.
Facile preparation of alkoxybenzoxazoles via direct SNAr on the benzoxazole ring
Germain, Hervé,Harris, Craig S.,Vautier, Michel,Warin, Nicolas
supporting information; experimental part, p. 554 - 556 (2010/10/02)
The synthesis of alkoxybenzoxazoles is in general quite challenging. During our investigation, we discovered that C-4 and C-7 fluoro precursors undergo SNAr with alkoxides affording moderate to excellent yields of substituted product.
Catalytic aza-Wittig cyclizations for heteroaromatic synthesis
Marsden, Stephen P.,McGonagle, Alison E.,McKeever-Abbas, Ben
supporting information; experimental part, p. 2589 - 2591 (2012/09/08)
The first examples of heterocycle synthesis by iminophosphorane formation/intramolecular aza-Wittig cyclizations that are catalytic in the organophosphorus component are reported. The reaction has been demonstrated in the synthesis of both azine (phenanthridine) and azole (benzoxazole) heterocycles. Catalyst loadings down to 1 mol % have been used with little or no loss in reaction efficiency. The intimate involvement of the phosphine oxide in the catalytic cycle has been verified by in situ infrared spectroscopy.
