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Functionalization by metallation of fluoropyrazine. Diazines XXI

✍ Scribed by Nelly Plé; Alain Turck; Arnault Heynderickx; Guy Quéguiner

Publisher
Elsevier Science
Year
1998
Tongue
French
Weight
830 KB
Volume
54
Category
Article
ISSN
0040-4020

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✦ Synopsis

Lithiation of fluoropyrazine followed by quenching with various electrophiles was successfully achieved and was used to synthesize new pyrazine derivatives. A further lithiation of 2fluoro-3-substituted pyrazines allowed access to 2,3,6-trisubstituted pyridazine derivatives. As an application, a one-pot synthesis of a quinuclidinylfluoropyrazine has been performed. When the 3substituent bears a TMS protected alcohol, functionalizatinn via metallation at C 5 position provides tetrasubstituted pyrazines in good yield.

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