164583-72-6Relevant academic research and scientific papers
Construction of anti-1,2-diols bearing chiral tertiary alcohol moiety using free hydroxyacetone as aldol donor by imidazole-based prolineamide catalyst
Guo, Wengang,Wei, Jianwei,Liu, Yan,Li, Can
, p. 6561 - 6568 (2015/03/30)
A direct aldol reaction of free hydroxyacetone and activated ketone has been firstly achieved with a newly developed imidazole-based prolineamide catalyst. The adducts anti-1,2-diols bearing a chiral tertiary alcohol moiety were obtained in high yield (up to 92%) and stereoselectivity (up to 15:1 dr and 90% ee).
Dienophilicity of imidazole in inverse electron demand Diels-Alder reactions: Cycloadditions with 1,2,4,5-tetrazines and the structure of zarzissine
Wan, Zhao-Kui,Woo, Grace H.C.,Snyder, John K.
, p. 5497 - 5507 (2007/10/03)
The inverse electron demand cycloadditions of 2-substituted imidazoles with dimethyl 1,2,4,5-tetrazine-3,6-dicarboxylate produced imidazo[4,5-d]pyridazines in good yields. This chemistry was applied to the synthesis of 2-amino-1H-imidazo[4,5-d]pyridazine (1), the structure reported for zarzissine, a cytotoxic marine alkaloid. Differences in the 1H- and 13C NMR spectra of 1 with those reported for zarzissine necessitated a structural revision, and zarzissine was then considered to be the corresponding 2-amino-1H-imidazo[4,5-b]pyrazine (2), which was subsequently synthesized from the parent heterocycle.
