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Titolo:
SYNTHESIS AND REGIOSELECTIVE HYDROLYSIS OF 2-IMIDAZOL-1-YLSUCCINIC ESTERS
Autore:
ZADERENKO P; GIL MS; BALLESTEROS P; CERDAN S;
Indirizzi:
UNIV NACL EDUC DISTANCIA,FAC CIENCIAS,DEPT QUIM ORGAN & BIOL,SENDA REY S-N E-28040 MADRID SPAIN UNIV NACL EDUC DISTANCIA,FAC CIENCIAS,DEPT QUIM ORGAN & BIOL E-28040 MADRID SPAIN CSIC,INST INVEST BIOMED,RESONANCIA MAGNET LAB E-28029 MADRID SPAIN
Titolo Testata:
Journal of organic chemistry
fascicolo: 21, volume: 59, anno: 1994,
pagine: 6268 - 6273
SICI:
0022-3263(1994)59:21<6268:SARHO2>2.0.ZU;2-T
Fonte:
ISI
Lingua:
ENG
Soggetto:
ACIDS;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Science Citation Index Expanded
Citazioni:
22
Recensione:
Indirizzi per estratti:
Citazione:
P. Zaderenko et al., "SYNTHESIS AND REGIOSELECTIVE HYDROLYSIS OF 2-IMIDAZOL-1-YLSUCCINIC ESTERS", Journal of organic chemistry, 59(21), 1994, pp. 6268-6273

Abstract

(+/-)-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 BAC(3) or BAL(1) mechanisms. Kinetic studies in H2O and D2O as well as O-18 and O-17 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.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 07/07/20 alle ore 11:42:12