jo501316m_si_001.cif (23.85 kB)
N‑Methylimidazole Promotes the Reaction of Homophthalic Anhydride with Imines
dataset
posted on 2015-12-17, 03:47 authored by Jian Liu, Zheng Wang, Aaron Levin, Thomas
J. Emge, Paul R. Rablen, David M. Floyd, Spencer KnappThe addition of N-methylimidazole (NMI) to the
reaction of homophthalic anhydride with imines such as pyridine-3-carboxaldehyde-N-trifluoroethylimine (9) reduces the amount
of elimination byproduct and improves the yield of the formal cycloadduct,
tetrahydroisoquinolonic carboxylate 10. 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 10 is also
described.
