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Synlett 2007(20): 3096-3102
DOI: 10.1055/s-2007-992384
DOI: 10.1055/s-2007-992384
ACCOUNT
© Georg Thieme Verlag Stuttgart · New York
Position-Flexible Elaboration of Halogenated Heterocycles: Metalated Species as Key Intermediates for Synthesis
Further Information
Received
18 September 2007
Publication Date:
03 December 2007 (online)
Publication History
Publication Date:
03 December 2007 (online)
Abstract
Halogens, in particular fluorine atoms, are favorite tools to fine-tune the chemical and biological properties of pharmaceutical or agricultural development products. At the same time, such an electronegative substituent can effectively assist the site-selective functionalization of an aromatic or heterocyclic core compound by directing a metal to the targeted position, the metal acting as a harbinger for the definitive substituent. The concept is illustrated by typical examples selected from the carbazole, indole, pyrrole, pyrazole, imidazole, pyridine, quinoline and pyrimidine fields.
1 Introduction
2 Carbazoles and Indoles
3 Pyrroles, Pyrazoles and Imidazoles
4 Pyridines, Quinolines and Pyrimidines
5 Conclusions and Outlook
Key Words
fluorine - functionalization - halogens - organometallic reagents - organic synthesis - regioselectivity
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Comprehensive Medicinal Chemistry
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