Determination of the Stereochemistry of Substituted 5-Methylenehydantoins and Thiohydantoins by 13C NMR and Homonuclear NOE Experiments

Autor: Fresneau, Patrick, Thomasson, François, Morand, Jean-Marc, Cussac, Max
Zdroj: Spectroscopy Letters; September 1993, Vol. 26 Issue: 8 p1511-1521, 11p
Abstrakt: Basically the aim of this work is to define the accurate configuration of the exocyclic double bond of substituted 5-methylenehydantoins and thiohydantoins which have been conceived as potential Aldose Reductase inhibitors. A previsional survey based upon the chemical shifts analysis from 1H and decoupled 13C NMR spectra discloses, for a part of the family of compounds, the assignment of the Zconfiguration for unsubstituted (2,3) and N-3 substituted (6,7,9) derivatives, and the E-configuration for the N-1 substituted (8,11) ones. The qualitative study with Homonuclear NOE (8,11) and the coupling constant measuring 3JC4-C=C-H6 from coupled 13C NMR (1-11), lead to the assignment of the accurate configuration of the whole family's compounds in agreement with the previsional study.
Databáze: Supplemental Index