Synthesis of functionalized pyrrole and indole derivatives through carbometallation of lithiated double bonds |
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Authors: | Fañanás F J Granados A Sanz R Ignacio J M Barluenga J |
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Institution: | Instituto Universitario de Química Organometálica Enrique Moles, Universidad de Oviedo, Spain. |
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Abstract: | 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 five-membered functionalized heterocycles. Although 2-lithioallylamines do not suffer intermolecular carbometallation, dimerization 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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