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.

Keywords

• Direct lithiation
• 5-lithiumindolizine
• 5-formylindolizine
• 5-iodoindolizine
• 5-benzoylindolizine
• Suzuki reaction
• reduction
• oxime.