Document Type
Article
Publication Date
8-15-2014
Published In
Journal Of Organic Chemistry
Abstract
The 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.
Recommended Citation
J. Liu, Z. Wang, A. Levin, T. J. Emge, Paul R. Rablen, D. M. Floyd, and S. Knapp.
(2014).
"N-Methylimidazole Promotes The Reaction Of Homophthalic Anhydride With Imines".
Journal Of Organic Chemistry.
Volume 79,
Issue 16.
7593-7599.
DOI: 10.1021/jo501316m
https://works.swarthmore.edu/fac-chemistry/196
Comments
This is an open access article published under an ACS AuthorChoice License, which permits copying and redistribution of the article or any adaptations for non-commercial purposes.