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

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

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Received: 23 April 2005; Accepted: 30 September 2005 / Published: 30 September 2005
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.
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.
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MDPI and ACS Style

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.

AMA Style

Kuznetsov AG, Bush AA, Rybakov VB, Babaev EV. An Improved Synthesis of Some 5-Substituted Indolizines Using Regiospecific Lithiation. Molecules. 2005; 10(9):1074-1083.

Chicago/Turabian Style

Kuznetsov, Alexey G.; Bush, Alexander A.; Rybakov, Viktor B.; Babaev, Eugene V. 2005. "An Improved Synthesis of Some 5-Substituted Indolizines Using Regiospecific Lithiation." Molecules 10, no. 9: 1074-1083.

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