Condensation reactions of guanidines with bis-electrophiles: Formation of highly nitrogenous heterocycles

Tetrahedron. 2013 Sep 9;69(36):7719-7731. doi: 10.1016/j.tet.2013.04.127.

Abstract

2-Amino-1,4-dihydropyrimidines were reacted with bis-electrophiles to produce novel fused bi-pyrimidine, pyrimido-aminotriazine, and pyrimido-sulfonamide scaffolds. In addition, a quinazoline library was constructed using a guanidine Atwal-Biginelli reaction with 1-(quinazolin-2-yl)guanidines. The product heterocycles have novel constitutions with high nitrogen atom counts and represent valuable additions to screening libraries for the discovery of new modulators of biological targets.

Keywords: Atwal-Biginelli reaction; Guanidines; Pyrimidines; Quinazolines; Screening library.