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Molecules 2005, 10(9), 1074-1083; doi:10.3390/10091074
Article

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

, ,  and *
Chemistry Department, Moscow State University, Moscow 119992, Russia
* Author to whom correspondence should be addressed.
Received: 23 April 2005 / Accepted: 30 September 2005 / Published: 30 September 2005
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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. Direct lithiation; 5-lithiumindolizine; 5-formylindolizine; 5-iodoindolizine; 5-benzoylindolizine; Suzuki reaction; reduction; oxime.
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Kuznetsov, A.G.; Bush, A.A.; Rybakov, V.B.; Babaev, E.V. An Improved Synthesis of Some 5-Substituted Indolizines Using Regiospecific Lithiation. Molecules 2005, 10, 1074-1083.

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