75470-88-1Relevant academic research and scientific papers
Preparative route to 2-ethoxycarbonylimidazole-4-phosphonate and diethyl imidazole-2,4-dicarboxylate
Vuilhorgne, Marc,Malpart, Joel,Mutti, Stephane,Mignani, Serge
, p. 159 - 162 (2007/10/03)
Practical synthesis of 2-ethoxycarbonylimidazole-4-phosphonate (1a) and diethyl imidazole-2,4-dicarboxylate (1b) are described.
Purines, Pyrimidines, and Imidazoles. Part 53. Synthesis of Some 5-Halogeno-analogues of Metiamide and Cimetidine
Brown, Tom,Shaw, Gordon,Durant, Graham J.
, p. 2310 - 2315 (2007/10/02)
Ethyl 5-chloroimidazole-4-carboxylate has been prepared by diazotisation of ethyl 5-amino-1-(di-O-isopropylidene-α- or α,β-D-mannofuranosyl)imidazole-4-carboxylate, reaction of the diazonium salt with copper(I) chloride and removal of the 1-substituent with hydrochloric acid, or by similar conversion of ethyl 5-amino-1-t-butylimidazole-4-carboxylate to ethyl 1-t-butyl-5-chloroimidazole-4-carboxylate, and removal of the t-butyl group with hydrogen bromide.Ethyl 5-fluoroimidazole-4-carboxylate has been prepared from ethyl 5-amino-1-t-butylimidazole-4-carboxylate by diazotisation and photolysis in the presence of tetrafluoroboric acid.Ethyl 5-chloroimidazole-4-carboxylate and ethyl 5-fluoroimidazole-4-carboxylate have been converted into the corresponding alcohols by reaction with lithium aluminium hydride. 5-Chloro-4-(hydroxymethyl)imidazole has also been prepared by electrolysis of 5-chloroimidazole-4-carboxylic acid at mercury cathode. 5-Chloroimidazole has been converted into the 5-chloroimidazolyl analogues of metiamide and cimetidine by a sequence of reactions, and 5-fluoroimidazole has been similarly converted into the 5-fluoro-analogue of metiamide.The metiamide and cimetidine analogues were found to be histamine H2-receptor antagonists.
