76182-29-1Relevant academic research and scientific papers
Carbene reactivity of 4-diazo-4H-imidazoles toward nucleophiles and aromatic compounds
Smith, Matthew R.,Blake, Alexander J.,Hayes, Christopher J.,Stevens, Malcolm F. G.,Moody, Christopher J.
experimental part, p. 9372 - 9380 (2010/03/04)
(Chemical Equation Presented) Carbenes derived from diazoimidazolecarboxylates 4 under thermal or photochemical conditions undergo O-H and N-H insertion reactions with alcohols and amines, respectively, in moderate yield, in competition with reduction in good H-donor solvents. Dichloromethane reacts to give the corresponding 4-chloroimidazole. Aromatic hydrocarbons are excellent traps for the imidazolylidene carbene and lead to a range of arylimidazole derivatives 7. Reaction with pyridine leads to the first example of a pyridinium ylide 8 formed from an imidazolylidene carbene, whereas irradiation in hexafluorobenzene gives the imidazoazocine 11, presumably by way of an initial norcaradiene intermediate.
Acid-base characteristics of 5-diazoimidazole derivatives
Mokrushin,Selezneva,Pospelova,Usova
, p. 1086 - 1091 (2007/10/03)
The transformation of 5-diazoimidazoles containing a carboxamide, ethoxycarbonyl, or nitro group at position 4 into diazonium salts was studied by UV and IR spectroscopy. It was shown by means of model compounds and chemical transformations that nitrosamines are involved in the transformation. 1998 Plenum Publishing Corporation.
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.
