Preparation of 1,2- and 1,4-dihydro derivatives of 6,7-dimethyl-2,3-diphenylquinoxaline via its dianion formed by reductive metallation


Kaban S., AYDOĞAN F.

MONATSHEFTE FUR CHEMIE, vol.139, no.6, pp.669-672, 2008 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 139 Issue: 6
  • Publication Date: 2008
  • Doi Number: 10.1007/s00706-007-0812-1
  • Journal Name: MONATSHEFTE FUR CHEMIE
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.669-672
  • Yıldız Technical University Affiliated: Yes

Abstract

Treatment of 6,7-dimethyl-2,3-diphenylquinoxaline with sodium in tetrahydrofuran formed a monomeric dianion. The chemical behavior of this dianion was investigated by a variety of reagents. As the result, alkylation reactions gave 1,2-dihydro derivatives, while acylation reactions occured at 1,4-positions. Annulation of the pyrazine ring system was accomplished by treating the dianion with oligomethylene dichlorides, Cl(CH(2))(n)Cl, n = 2-4.