SYNTHESIS AND PROPERTIES OF 6-AMINO-7-HETARYL-5-R-5H-PYRROLO[2,3-<i>b</i>]PYRAZINE-2,3-DICARBONITRILES

Abstract

We have established that when 5-chloro-6-[cyano(2,3-dihydro-1-R-benzo[d]azol-2-yl)methyl]-2,3-pyrazinedicarbonitriles are reacted with nucleophilic reagents (aliphatic and aromatic amines, hydrogen sulfide), annelation of the five-membered ring occurs on the [b] face of the pyrazine with formation of 6-amino-7-hetaryl-5-R-5H-pyrrolo[2,3-b]pyrazine-2,3-dicarbonitriles and 6-amino-7-(1H-benzo[d]imidazol-2-yl)thieno[2,3-b]pyrazine-2,3-dicarbonitrile respectively. Further heating with excess of acylating reagent leads to formation of a novel heterocyclic system 1H-benzo[4,5]imidazo[1,2-c]pyrazino[2',3':4,5]pyrrolo[3,2-e]pyrimidine. Reaction of vicinal dinitriles with hydrazine hydrate leads to the novel system 1H-pyrrolo[2',3':5,6]pyrazino[2,3-d]pyridazine.

How to Cite
Volovenko, Yu. M.; Dubinina, G. G. Chem. Heterocycl. Compd. 2002, 38, 336. [Khim. Geterotsikl. Soedin. 2002, 372.]

For this article in the English edition, see DOI https://doi.org/10.1023/A:1015695522610