Nickel-catalyzed denitrogenative annulation reactions of 1,2,3-Benzotriazin-4(3 H)-ones with 1,3-dienes and alkenes

Tomoya Miura, Masao Morimoto, Motoshi Yamauchi, Masahiro Murakami

Research output: Contribution to journalArticlepeer-review

48 Citations (Scopus)

Abstract

(Figure presented) 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.

Original languageEnglish
Pages (from-to)5359-5362
Number of pages4
JournalJournal of Organic Chemistry
Volume75
Issue number15
DOIs
Publication statusPublished - Aug 6 2010
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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