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Reductive metallation of 6‐methyl‐2,3‐diphenylquinoxaline. Synthesis of 1,4‐dihydro‐1,4‐diazine derivatives
Author(s) -
Öcal Nüket,
Turgut Zuhal,
Kaban Şniz
Publication year - 1998
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570350620
Subject(s) - chemistry , pyrazine , annulation , tetrahydrofuran , diazine , reagent , alkylation , adduct , medicinal chemistry , ring (chemistry) , nucleophile , organic chemistry , catalysis , solvent
The reductive metallation of 6‐methyl‐2,3‐diphenylquinoxaline 1 with sodium metal in tetrahydrofuran and inert atmosphere to a monomeric dianion 2 has been explored and the nucleophilicity of this disodium adduct was investigated with various alkylation and acylation reagents. An annulation of the pyrazine ring system was accomplished by treating the dianion with polymethylene chlorides, Cl(CH 2 ) n Cl, n = 3,4.