721-89-1Relevant articles and documents
Straightforward access to (imidazol-2-yl)acetates by reaction of 2-unsubstituted imidazole 3-oxides with dimethyl acetylenedicarboxylate
Mlostoń, Grzegorz,Jasiński, Marcin,Heimgartner, Heinz
, p. 2542 - 2547 (2011/05/16)
A new method for the preparation of 1,4,5-trisubstituted (imidazol-2-yl)acetates, based on the reaction of the corresponding imidazole 3-oxides with dimethyl acetylenedicarboxylate (DMAD) is described. Formation of the products is rationalized by a formal 1,3-dipolar cycloaddition and subsequent oxaloyl cleavage. 1,4,5-Trisubstituted imidazole 3-oxides bearing an electron-withdrawing substituent at C(4), easily react with dimethyl acetylenedicarboxylate (DMAD), yielding the corresponding oxobutanoates, which subsequently, in a one-pot procedure undergo hydrolysis through an "oxaloyl cleavage" mode. New (imidazol-2-yl)acetates were isolated in high yields. Copyright