title: An improved synthesis of some 5-substituted indolizines using regiospecific lithiation.
abstract: Various 2-substituted indolizines can be directly and selectively lithiated in the 5 position and subsequent reactions with different electrophiles lead to some novel classes of indolizines. In particular, previously unknown 5-formyl- and 5-iodoindolizine have been prepared by this way and the molecular structure of 5-formyl-2- phenylindolizine was confirmed by X-Ray analysis. The reactivity of the 5-CHO- and 5- COPh groups toward some nucleophiles has been examined, and some additional classes of derivatives (oximes and alcohols) have been obtained. The possibility of Suzuki cross- coupling of 5-iodoindolizines and boronic acids was proven.
authors.affiliation: Chemistry Department, Moscow State University, Moscow 119992, Russia.
authors.forename: Alexey G
authors.initials: AG
authors.lastname: Kuznetsov
authors.forename: Alexander A
authors.initials: AA
authors.lastname: Bush
authors.forename: Viktor B
authors.initials: VB
authors.lastname: Rybakov
authors.forename: Eugene V
authors.initials: EV
authors.lastname: Babaev
mesh_terms: D007212:Indolizines / Q000138:chemical synthesis* / Q000737:chemistry; D008094:Lithium / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D011522:Protons; D013237:Stereoisomerism
chemical_list: D007212:Indolizines; D011522:Protons; D008094:Lithium