title: The Aryne aza-Diels-Alder Reaction: Flexible Syntheses of Isoquinolines.
abstract: Two cascade reactions have been developed for the time-efficient preparation of a variety of functionalized aromatic heterocyclic products exhibiting an isoquinoline core. The approach is based on the normal electron-demand [4 + 2] aza-Diels-Alder cycloaddition of electron-rich N-aryl imines with arynes. Using this strategy, an expeditious total synthesis of the naturally occurring benzo[c]phenanthridine alkaloid nornitidine was achieved.
authors.affiliation: †Aix Marseille Université, Centrale Marseille, CNRS, iSm2 UMR 7313, 13397, Marseille, France.
authors.forename: Juan-Carlos
authors.initials: JC
authors.lastname: Castillo
authors.affiliation: ‡Universidad del Valle, Departamento de Química, A.A. 25360, Cali, Colombia.
authors.forename: Jairo
authors.initials: J
authors.lastname: Quiroga
authors.affiliation: ‡Universidad del Valle, Departamento de Química, A.A. 25360, Cali, Colombia.
authors.forename: Rodrigo
authors.initials: R
authors.lastname: Abonia
authors.affiliation: †Aix Marseille Université, Centrale Marseille, CNRS, iSm2 UMR 7313, 13397, Marseille, France.
authors.forename: Jean
authors.initials: J
authors.lastname: Rodriguez
authors.affiliation: †Aix Marseille Université, Centrale Marseille, CNRS, iSm2 UMR 7313, 13397, Marseille, France.
authors.forename: Yoann
authors.initials: Y
authors.lastname: Coquerel
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D001551:Benz(a)Anthracenes / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D061565:Cycloaddition Reaction; D007097:Imines / Q000138:chemical synthesis; D007546:Isoquinolines / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D001551:Benz(a)Anthracenes; D007097:Imines; D007546:Isoquinolines; C000602500:nornitidine