Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 75, Issue 15, Pages 5359-5362Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo1008756
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Funding
- MEXT [20037032]
- Mitsubishi Chemical Corporation
- Sumitomo Foundation
- Astellas Award in Synthetic Organic Chemistry, Japan
- Grants-in-Aid for Scientific Research [20037032] Funding Source: KAKEN
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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.
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