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ChemInform Abstract: Aza-Indolizine with Bridgehead Nitrogen. Metalation, Halogen-Metal Exchange and Directed ortho-Lithiation in the Imidazo[1,2-a]pyrazine Series.

✍ Scribed by O. VITSE; J. BOMPART; G. SUBRA; H. VIOLS; R. ESCALE; J. P. CHAPAT; P. A. BONNET

Publisher: John Wiley and Sons
Year: 2010
Weight: 36 KB
Volume: 29
Category: Article
ISSN: 0931-7597
DOI: 10.1002/chin.199838184

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✦ Synopsis

Aza-Indolizine with Bridgehead Nitrogen. Metalation, Halogen-Metal Exchange and Directed ortho-Lithiation in the Imidazo[1,2-a]pyrazine Series.

-Functionalizations of some imidazo[1,2-a]pyrazine derivatives via metalation and halogen-metal exchange reactions are investigated. Bromine substituents are found to exhibit different behavior in lithiation reactions depending on their positions at the heterocycle. Halogen-metal exchange is observed with the bromine at position 3, while bromine at position 6 leads to functionalization at C-5 due to an ortho-directing effect.

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