The Rh2(OAc)4-catalyzed reactions of diazoacetates with diisopropylcyanamide gave 5-alkoxy-2-aminooxazoles. Their isolation was achieved by introduction of a bulky alkoxy group at 5-position. The 5-alkoxy-2-aminooxazole reacted with methanol to give a 1 : 1-adduct in a quantitative yield. The kinetic study indicates that this reaction proceeds in a stepwise mechanism including an equilibrium of the 5-alkoxy-2-aminooxazole with a nitrile ylide intermediate.

5-alkoxy-2-aminooxazoles can be isolated and reacted with methanol in a stepwise mechanism, resulting in a 1:1 adduct with a nitrile ylide intermediate.

Paper

Formation of 5-Alkoxy-2-aminooxazoles and Their Novel Reactivity: Equilibrium with Nitrile Ylide

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