- Synthesis and regioselective hydrolysis of 2-imidazol-1-ylsuccinic esters
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(±)-2-Imidazol-1-ylsuccinic esters were synthesized by thermal addition of imidazole to either fumaric or maleic esters. Acceleration of the reaction was achieved, in some cases, using microwave heating. These esters underwent an easy regioselective hydrolysis, under neutral conditions, to give the corresponding half-esters: (±)-3-(alkoxycarbonyl)-2-imidazol-1-ylpropionic acids, through either BAC3 or BAL1 mechanisms. Kinetic studies in H2O and D2O as well as 18O and 17O labeling experiments supported the proposed mechanism. The results of these hydrolyses, which depended on the nature of the alcohol moiety, were compared with those obtained with some imidazol-1-ylacetate analogues or with (±)-2-pyrazol-1-yl- and benzimidazol-1-ylsuccinic esters. In general, imidazolylsuccinic esters hydrolyzed faster than the homologous derivatives from pyrazole or benzimidazole.
- Zaderenko,Gil,Ballesteros,Cerdan
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- A PROCESS FOR THE PREPARATION OF 2-(IMIDAZOL-1-YL)-1-HYDROXYETHANE-1, 1-DIPHOSPHONIC ACID
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The present invention provides a process for preparation of 2-(imidazol-1-yl)-1-hydroxyethane-1,1-diphosphonic acid, compound of formula (1), said process comprising (a) reacting imidazole with chloroacetyl chloride and benzyl alcohol in homogenous system in one pot to obtain benzyl 1-imidazolylacetate, compound of formula (3); (b) debenzylating benzyl 1-imidazolylacetate, a compound of formula (3) to imidazole 1-ylacetic acid, compound of formula (2) and (c) converting compound of formula (2) to compound of formula (1).
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(2008/06/13)
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