P. Zaderenko et al., SYNTHESIS AND REGIOSELECTIVE HYDROLYSIS OF 2-IMIDAZOL-1-YLSUCCINIC ESTERS, Journal of organic chemistry, 59(21), 1994, pp. 6268-6273
(+/-)-2-Imidazol-1-ylsuccinic esters were synthesized by thermal addit
ion of imidazole to either fumaric or maleic esters. Acceleration of t
he reaction was achieved, in some cases, using microwave heating. Thes
e esters underwent an easy regioselective hydrolysis, under neutral co
nditions, to give the corresponding half-esters: (+/-)-3-(alkoxycarbon
yl)-2-imidazol-1-ylpropionic acids, through either BAC(3) or BAL(1) me
chanisms. Kinetic studies in H2O and D2O as well as O-18 and O-17 labe
ling experiments supported the proposed mechanism. The results of thes
e 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. I
n general, imidazolylsuccinic esters hydrolyzed faster than the homolo
gous derivatives from pyrazole or benzimidazole.