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.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
REFERENCES
Yu. M. Volovenko and G. G. Dubinina, Khim. Geterotsikl. Soedin., 1234 (1999).
Yu. M. Volovenko and G. G. Dubinina, Khim. Geterotsikl. Soedin., in press.
B. Pilarski and H. Foks, Polish Patent 135250; Chem. Abstr., 113, 172054 (1990).
Yu. M. Volovenko, G. G. Dubinina, T. V. Shokol, and F. S. Babichev, Dokl. Akad. Nauk Ukraine, No. 10, 126 (1994).
T. Suzuki, Y. Nagae, and K. Mitsuhashi, J. Heterocycl. Chem., 23, 1419 (1986).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Volovenko, Y.M., Dubinina, G.G. Synthesis of 6-Amino-5-R2-7-(6-R1-4-oxo-3,4-dihydro-2-quinazolyl)-5H-pyrrolo[2,3-b]pyrazine-2,3-dicarbonitriles. Chemistry of Heterocyclic Compounds 38, 219–225 (2002). https://doi.org/10.1023/A:1015399511473
Issue Date:
DOI: https://doi.org/10.1023/A:1015399511473