SYNTHESIS OF 6-AMINO-5-R²-7-(6-R¹-4-OXO-3,4-DIHYDRO-2-QUINAZOLYL)-5H-PYRROLO[2,3-<i>b</i>]-PYRAZINE-2,3-DICARBONITRILES

Abstract

It has been found that malonodinitrile and 2-(6-R¹-oxo-3,4-dihydro-2-quinazolyl)acetonitrile in the presence of triethylamine undergo hetarylation by 5,6-dichloro-2,3-pyrazinedicarbonitrile at the active methylene group to give the triethylammonium salt of 2-(3-chloro-5,6-dicyano-2-pyrazinyl)malononitrile or 5-chloro-6-cyano(6-R¹-4-oxo-1,2,3,4-tetrahydro-2-quinazolylidene)methyl-2,3-pyrazinedicarbonitriles. Reaction of these with primary amines leads to annelation of the pyrrole ring at the pyrazine [b] edge to give 6-amino-5-R-5H-pyrrolo[2,3-b]pyrazine-2,3,7-tricarbonitriles and 6-amino-5-R²-7-(6-R¹-4-oxo-3,4-dihydro-2-quinazolyl)-5H-pyrrolo[2,3-b]pyrazine-2,3-dicarbonitriles respectively.

How to Cite
Volovenko, Yu. M.; Dubinina, G. G. Chem. Heterocycl. Compd. 2002, 38, 219. [Khim. Geterotsikl. Soedin. 2002, 241.]

For this article in the English edition, see DOI https://doi.org/10.1023/A:1015399511473