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Aza-indolizine with bridgehead nitrogen. Metalation, halogen-metal exchange and directed ortho-lithiation in the imidazo[1,2-a]pyrazine series

✍ Scribed by Olivier Vitse; Jacques Bompart; Guy Subra; Henri Viols; Roger Escale; Jean P. Chapat; Pierre A. Bonnet

Book ID
104208583
Publisher
Elsevier Science
Year
1998
Tongue
French
Weight
605 KB
Volume
54
Category
Article
ISSN
0040-4020

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✦ Synopsis

The n-BuLi and lithium 2,2,6,6-tetramethylpiperidine (LTMP) metalation of imidazo[l,2..alpyrazine heterocycles and subsequent quenching with electrophiles is described. Bromine atoms exhibit different behaviours towards lithiation depending on their positions (3 or 6) on the imidazo[1,2-a]pyrazine heterocycle. Halogen-metal exchange occurs readily with the bromine on position 3. On the contrary, bromine on position 6 only leads to C-5 substituted derivatives further to an ortho-directing effect.

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ChemInform Abstract: Aza-Indolizine with
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📂 Article 📅 1997 🏛 American Chemical Society 🌐 English ⚖ 165 KB