Synthesis and regioselective hydrolysis of 2-imidazol-1-ylsuccinic esters

Article abstract of DOI:10.1021/jo00100a030

(±)-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.

Full text of DOI:10.1021/jo00100a030

Evaluation Only. Created with Aspose.PDF. Copyright 2002-2021 Aspose Pty Ltd.

Evaluation Only. Created with Aspose.PDF. Copyright 2002-2021 Aspose Pty Ltd.

Evaluation Only. Created with Aspose.PDF. Copyright 2002-2021 Aspose Pty Ltd.

Evaluation Only. Created with Aspose.PDF. Copyright 2002-2021 Aspose Pty Ltd.