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Article 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.
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Source |
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| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4136697 | PMC |
| http://dx.doi.org/10.1021/jo501316m | DOI Listing |
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