title: N-methylimidazole promotes the reaction of homophthalic anhydride with imines.
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.
authors.affiliation: Department of Chemistry & Chemical Biology, Rutgers The State University of New Jersey , 610 Taylor Road, Piscataway, New Jersey 08854, United States.
authors.forename: Jian
authors.initials: J
authors.lastname: Liu
authors.forename: Zheng
authors.initials: Z
authors.lastname: Wang
authors.forename: Aaron
authors.initials: A
authors.lastname: Levin
authors.forename: Thomas J
authors.initials: TJ
authors.lastname: Emge
authors.forename: Paul R
authors.initials: PR
authors.lastname: Rablen
authors.forename: David M
authors.initials: DM
authors.lastname: Floyd
authors.forename: Spencer
authors.initials: S
authors.lastname: Knapp
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D002264:Carboxylic Acids / Q000737:chemistry*; D007093:Imidazoles / Q000737:chemistry*; D007097:Imines / Q000737:chemistry*; D007546:Isoquinolines / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D010796:Phthalic Anhydrides / Q000737:chemistry*; D011725:Pyridines / Q000737:chemistry*
chemical_list: D000447:Aldehydes; D002264:Carboxylic Acids; D007093:Imidazoles; D007097:Imines; D007546:Isoquinolines; D010796:Phthalic Anhydrides; D011725:Pyridines; C000595169:pyridine-3-carboxaldehyde-N-trifluoroethylimine; C018100:1-methylimidazole