An Improved Synthesis of Some 5-Substituted Indolizines Using Regiospecific Lithiation

Molecules

Alexey G. Kuznetsov¹  Alexander A. Bush¹  Viktor B. Rybakov¹ 

[1] id="af1-molecules-10-01074">Chemistry Department, Moscow State University, Moscow 119992, Russ

关键词: Direct lithiation;    5-lithiumindolizine;    5-formylindolizine;    5-iodoindolizine;    5‑benzoylindolizine;    Suzuki reaction;    reduction;    oxime;   

DOI  :  10.3390/10091074

来源: mdpi

【 摘 要 】

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.

【 授权许可】

Unknown   
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