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Synthesis of Functionalized Pyrrole and Indole Derivatives through Carbometallation of Lithiated Double Bonds
Author(s) -
Fañanás Francisco J.,
Granados Alejandro,
Sanz Roberto,
Ignacio José M.,
Barluenga José
Publication year - 2001
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/1521-3765(20010702)7:13<2896::aid-chem2896>3.0.co;2-r
Subject(s) - electrophile , tetramethylethylenediamine , chemistry , intramolecular force , indole test , intermolecular force , pyrrole , double bond , reagent , zirconium , medicinal chemistry , combinatorial chemistry , polymer chemistry , organic chemistry , molecule , catalysis
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.