72511-04-7Relevant articles and documents
α-Nitro Ketones and Esters from Acylimidazoles
Crumbie, Robyn L.,Nimitz, Jonathan S.,Mosher, Harry S.
, p. 4040 - 4045 (2007/10/02)
The anion of 2-(2-nitroethyl)-1,3-dioxolane (4), prepared from the corresponding 2-bromo compound (3), undergoes condensation with acylimidazoles to give the 3-nitro-4-oxobutanal acetals (9), which can serve as valuable polyfunctional intermediates.Condensation with 1-(methoxyoxalyl)imidazole gives the tetrafunctionalized methyl 4-(1,3-dioxolan-2-yl)-3-nitro-2-oxobutanoate (13), which, however, decomposed on attempted deprotection of the ester function.The syntheses in excellent yields of simple α-nitro ketones and α-nitro esters from acylimidazoles and nitroethane and 2-nitropropane are also described.
