Journal Article

·1996

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

Şeniz Kaban YTU , Nüket Öcal YTU

Recueil des Travaux Chimiques des Pays-Bas

Abstract

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.

Keywords

Chemistry Pyrazine Diazine Ethyl chloroformate Methyl iodide Alkylation Medicinal chemistry Adduct Tetrahydrofuran Alkali metal Annulation Acylation Protonation Benzoyl chloride Organic chemistry Chloride Reagent Catalysis

Subject Areas

Synthesis and Biological Evaluation ·Organic Chemistry ·Physical Sciences
Chemical Synthesis and Analysis ·Molecular Biology ·Life Sciences
Oxidative Organic Chemistry Reactions ·Organic Chemistry ·Physical Sciences

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