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Synthesis of Functionalized Pyrrole and Indole Derivatives through Carbometallation of Lithiated Double Bonds

✍ Scribed by Francisco J. Fañanás; Alejandro Granados; Roberto Sanz; José M. Ignacio; José Barluenga

Publisher
John Wiley and Sons
Year
2001
Tongue
English
Weight
202 KB
Volume
7
Category
Article
ISSN
0947-6539

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✦ Synopsis

Bis(2-lithioallyl)amines derived from bis(2-bromoallyl)amines undergo intramolecular carbometallation of a lithiated double bond, giving dilithiated dihydropyrroles. The cyclizations are promoted by N,N,N',N'-tetramethylethylenediamine (TMEDA). Reaction of these intermediates with electrophiles allows the preparation of some new fused and nonfused fivemembered functionalized heterocycles. Although 2-lithioallylamines do not suffer intermolecular carbometallation, di-merization products are obtained with their copper or zirconium derivatives. Finally, the application of this new reaction to 2-lithio-N-(2-lithioallyl)anilines leads to 3-lithiomethylindole derivatives, which are transformed to functionalized indole derivatives by reaction with electrophiles.

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ChemInform Abstract: Synthesis of Functi
ChemInform Abstract: Synthesis of Functionalized Pyrrole and Indole Derivatives Through Carbometalation of Lithiated Double Bonds.
✍ Francisco J. Fananas; Alejandro Granados; Roberto Sanz; Jose M. Ignacio; Jose Ba 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 38 KB 👁 1 views

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