Synthesis and N-Alkylation of 2-Alkyl-and 2-AryIimidazole-4,5-dicarboxylic Acid Esters

摘要

Nitration of D-tartaric acid,followed by treatment of the resulting dinitrotartaric acid with ammonia and aldehydes gave 2-phenyl-,2-(2-pyridyl)-,2-isopropyl-,and 2-isobutylimidazole-4,5-dicarboxylic acids.Some factors affecting the yield of the final products were revealed,and optimal conditions for their esterification were found.N-Alkylation of 2-substituted imidazole-4,5-dicarboxylates thus obtained involves considerable steric hindrances;therefore,the corresponding N-alkyl derivatives can be obtained in a poor yield only in the presence of such a strong base as l,8-diazabicyclo[5.4.0]undec-7-ene.