Synthesis of symmetric bis(imidazole-4,5-dicarboxamides) substituted with amino acids.
A series of symmetric bis(imidazole-4,5-dicarboxamides) (bis-I45DCs) were prepared with amino acid esters and a variety of linker groups. The critical pyrazine intermediates, substituted with amino acid esters, were synthesized by stoichiometric control of the amino acid ester, even though primary alkanamines, in comparison, generally offer less selectivity for this reaction. Diamines are added to subsequently react with and open the remaining acyl imidazole bonds in the pyrazine intermediates and thereby yield the bis-I45DCs.
Wiznycia
Alexander V
AV
Department of Chemistry, Kansas State University, Manhattan, Kansas 66506, USA.
Rush
Jeremy R
JR
Baures
Paul W
PW
D000577:Amides / Q000138:chemical synthesis*; D000596:Amino Acids / Q000138:chemical synthesis / Q000737:chemistry*; D007093:Imidazoles / Q000138:chemical synthesis*; D015394:Molecular Structure; D013237:Stereoisomerism
D000577:Amides; D000596:Amino Acids; D007093:Imidazoles