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Interaction of alkali metals with unsaturated heterocyclic compounds. The reductive metallation of 2,3,5,6-tetraphenylpyrazine and the synthesis of 1,2-dihydro-1,4-diazine derivatives

✍ Scribed by Şeniz Kaban; Nüket Öcal

Publisher: Elsevier Science
Year: 2010
Tongue: English
Weight: 458 KB
Volume: 115
Category: Article
ISSN: 0165-0513
DOI: 10.1002/recl.19961150707

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✦ Synopsis

Abstract

Treatment of 2,3,5,6‐tetraphenylpyrazine (1) with sodium in tetrahydrofuran effected the formation of monomeric dianion 2. The chemical behaviour of this new disodium adduct was characterized by a variety of reagents. Generally, the protonation (water), alkylation (methyl iodide and benzyl chloride), and acylation (methyl and ethyl chloroformate) products were 1,2‐dihydrotetraphenyldiazine derivatives. An annulation of the pyrazine ring system was accomplished by treating the dianion with polymethylene chlorides, Cl(CH~2~)~n~Cl, n = 2, 3, 4.

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