Liu, Jian Wang, Zheng Levin, Aaron Emge, Thomas J. Rablen, Paul R. Floyd, David M. Knapp, Spencer <i>N</i>‑Methylimidazole Promotes the Reaction of Homophthalic Anhydride with Imines The addition of <i>N</i>-methylimidazole (NMI) to the reaction of homophthalic anhydride with imines such as pyridine-3-carboxaldehyde-<i>N</i>-trifluoroethylimine (<b>9</b>) reduces the amount of elimination byproduct and improves the yield of the formal cycloadduct, tetrahydroisoquinolonic carboxylate <b>10</b>. Carboxanilides of such compounds are of interest as potential antimalarial agents. A mechanism that rationalizes the role of NMI is proposed, and a gram-scale procedure for the synthesis and resolution of <b>10</b> is also described. elimination byproduct;antimalarial agents;homophthalic anhydride;imine;mechanism;role;Promote;pyridine;compound;cycloadduct;rationalize;Homophthalic Anhydride;IminesThe addition;tetrahydroisoquinolonic carboxylate 10. Carboxanilides;synthesis;procedure;NMI 2015-12-17
    https://acs.figshare.com/articles/dataset/_i_N_i_Methylimidazole_Promotes_the_Reaction_of_Homophthalic_Anhydride_with_Imines/2037924
10.1021/jo501316m.s001