Mono- and dialkylations of pyrrole at C2 and C5 positions by nucleophilic substitution reaction in ionic liquid.
[reaction: see text] A novel ionic liquid methodology for pyrrole C-alkylation is described. The pyrrole alkylation is achieved with various simple alkyl halides and mesylates selectively at C2 and C5 positions in good yields with minimal byproducts under relatively mild conditions in various ionic liquids. 2-(3-Phenylpropyl)pyrrole (2a) was synthesized from pyrrole and 1-bromo-3-phenylpropane in a mixture solvent system, [bmim][SbF6] and CH3CN, in 81% yield at 115 degrees C for 44 h with 5% yield of dialkylated compound 3a.
Jorapur
Yogesh R
YR
Department of Chemistry, Inha University, 253 Yonghyundong Namgu, Inchon, 402-751 Korea.
Lee
Chang-Hee
CH
Chi
Dae Yoon
DY