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We have studied the structure (isomerism and conformation) of the products resulting from the double addition of four NH-azoles, benzotriazole, pyrazole, imidazole and benzimidazole, on glyoxal and on DODO ([1,4]-dioxane-2,3-diol). The reactions result in the formation of meso and d,l diastereoisomers, although in all cases a significant amount of unreacted azole remains. The four component mixtures were analyzed by 1 H and 13 C NMR. DFT calculations (B3LYP/631G*) were carried out to determine the relative stabilities of the different structures.

Double addition of azoles to glyoxal: characterization of the bis-adducts and theoretical study of their structure