title: Nickel-catalyzed denitrogenative annulation reactions of 1,2,3-benzotriazin-4(3H)-ones with 1,3-dienes and alkenes.
abstract: 1,2,3-Benzotriazin-4(3H)-ones react with 1,3-dienes in the presence of a nickel(0)/phosphine complex to give a variety of 3,4-dihydroisoquinolin-1(2H)-ones. Oxidative insertion of nickel(0) into the triazinone moiety prompts extrusion of dinitrogen to give a five-membered ring azanickelacyclic intermediate. Subsequent insertion of 1,3-dienes into the nickel-carbon bond followed by allylic amidation affords 3,4-dihydroisoquinolin-1(2H)-ones. Alkenes also undergo insertion into the five-membered ring azanickelacyclic intermediate, and subsequent reductive elimination gives 3-substituted 3,4-dihydroisoquinolin-1(2H)-ones.
authors.affiliation: Department of Synthetic Chemistry and Biological Chemistry, Kyoto University, Katsura, Kyoto 615-8510, Japan.
authors.forename: Tomoya
authors.initials: T
authors.lastname: Miura
authors.forename: Masao
authors.initials: M
authors.lastname: Morimoto
authors.forename: Motoshi
authors.initials: M
authors.lastname: Yamauchi
authors.forename: Masahiro
authors.initials: M
authors.lastname: Murakami