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

doi:10.3390/10091074

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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

Alexey G. Kuznetsov, Alexander A. Bush, Viktor B. Rybakov and Eugene V. Babaev *

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

(This article belongs to the Special Issue Selected Papers from the “2nd International Conference on Natural Products and Physiologically Active Substances” (ICNPAS-2004) and the 3rd EuroAsian Heterocyclic Meeting “Heterocycles in Organic and Combinatorial Chemistry”)

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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.

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Cite This Article

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 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(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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