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

• DOI: 10.1016/j.tet.2013.04.127
• Publication Date: 2013-05-01T21:37:45Z
• Authors: David M. Arnold; Matthew G. LaPorte; Shelby M. Anderson; Peter Wipf
• Keywords: Guanidine; Quinazoline; Nitrogen atom; Sulfonamide

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.