期刊
SYNTHESIS-STUTTGART
卷 51, 期 20, 页码 3815-3824出版社
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0037-1611882
关键词
homophthalimides; diazo compounds; arylation; Friedel-Crafts reaction; monofluorination; fluorohalogenation; Bronsted acids; isoquinoline-1,3(2H,4H)-dione
资金
- Russian Science Foundation [18-13-00008]
- Russian Science Foundation [19-75-30008, 18-13-00008] Funding Source: Russian Science Foundation
Protonation of 4-diazoisoquinoline-1,3(2 H ,4 H )-diones in Bronsted acids gives rise to diazonium cations that can be trapped with arenes to give 4-arylisoquinoline-1,3(2 H ,4 H )-diones (homophthalimides). This provides a new, metal-free approach to 4-aryltetrahydroisoquinolines (obtainable from respective homophthalimides by reduction). Similarly, a fluorine atom can be introduced by trapping the diazonium cation with HF. This led to the preparation of the first examples of 4-monofluoro-substituted isoquinoline-1,3-diones (as well as their 4-bromo-4-fluoro and 4-chloro-4-fluoro variants), important carboxylic acid isosteres on their own and precursors of useful 4-fluorotetrahydroisoquinoline building blocks.
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