INTERACTION OF ALKALI-METALS WITH UNSATURATED HETEROCYCLIC-COMPOUNDS - THE REDUCTIVE METALATION OF 2,3,5,6-TETRAPHENYLPYRAZINE AND THE SYNTHESIS OF 1,2-DIHYDRO-1,4-DIAZINE DERIVATIVES

Authors
Citation
S. Kaban et N. Ocal, INTERACTION OF ALKALI-METALS WITH UNSATURATED HETEROCYCLIC-COMPOUNDS - THE REDUCTIVE METALATION OF 2,3,5,6-TETRAPHENYLPYRAZINE AND THE SYNTHESIS OF 1,2-DIHYDRO-1,4-DIAZINE DERIVATIVES, Recueil des travaux chimiques des Pays-Bas, 115(7-8), 1996, pp. 377
Citations number
14
Language
INGLESE
art.tipo
Article
Categorie Soggetti
Chemistry
ISSN journal
0165-0513
Volume
115
Issue
7-8
Year of publication
1996
Database
ISI
SICI code
0165-0513(1996)115:7-8<377:IOAWUH>2.0.ZU;2-E
Abstract
Treatment of 2,3,5,6-tetraphenylpyrazine (1) with sodium in tetrahydro furan effected the formation of monomeric dianion 2. The chemical beha viour of this new disodium adduct was characterized by a variety of re agents. Generally, the protonation (water), alkylation (methyl iodide and benzyl chloride), and acylation (methyl and ethyl chloroformate) p roducts were 1,2-dihydrotetraphenyldiazine derivatives. An annulation of the pyrazine ring system was accomplished by treating the dianion w ith polymethylene chlorides, Cl(CH2)(n)Cl, n = 2, 3, 4.