H. Rutner, P. Spoerri
Dec 1, 1966
Citations
0
Influential Citations
21
Citations
Journal
Journal of Heterocyclic Chemistry
Abstract
An improved method for the preparation of fluoropyrazine (I) by halogen exchange and a synthesis of 2-fluoroquinoxaline (II) by a Balz-Schiemann reaction are presented. Compound I hydrolyzes slowly in 0.01N sodium hydroxide, rapidly in 1.07N sodium hydroxide at 26.00°. Compound II hydrolyzes 240 times faster than I in 0.01N sodium hydroxide at 26.00°. Hydrolysis of I in 6N hydrochloric acid at room temperature is slow. Compound I underwent nucleophilic reactions with formation of hydroxy, amino, methylamino, piperidino, benzylamino and anilinopyrazines. Pyrazinesulfonic acid was obtained from I and sodium sulfite and tetrazolo[1, 5-a]pyrazine (IV), a novel ring system, from I and sodium azide.