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Palladium-Catalysed Synthesis of Dibenzo[de,g]quinolines. A Novel Approach to the B-Ring System of Aporphine-Related Heterocycles

✍ Scribed by Anne-Elisabeth Gies; Michel Pfeffer; Claude Sirlin; John Spencer

Publisher: John Wiley and Sons
Year: 1999
Tongue: English
Weight: 254 KB
Volume: 1999
Category: Article
ISSN: 1434-193X
DOI: 10.1002/(sici)1099-0690(199908)1999:8<1957::aid-ejoc1957>3.0.co;2-i

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✦ Synopsis

Dibenzo[de,g]quinolines 5 were formed by the palladium-nes led to high levels of regioselectivity. These reactions constitute a new synthesis of the B-ring system of catalysed heteroannulation of disubstituted alkynes and 1iodo-10-(dimethylamino)phenanthrene (3c). Symmetric alky-aporphine heterocycles.

served in the insertion of disymmetric alkynes and the in Scheme 1

Key features of this protocol, which involves the formation of both a CϪC and a CϪN bond, include the favour-Scheme 3 able yields obtained for alkynes containing aryl or electronwithdrawing groups, the high level of regioselectivity ob-

The benzo[d,e]quinolines, 2 depicted above effectively [

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ChemInform Abstract: Palladium-Catalyzed

ChemInform Abstract: Palladium-Catalyzed Synthesis of Dibenzo[de,g]quinolines. A Novel Approach to the B-Ring System of Aporphine-Related Heterocycles.

✍ Anne-Elisabeth Gies; Michel Pfeffer; Claude Sirlin; John Spencer 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 32 KB 👁 1 views