21761-80-8Relevant academic research and scientific papers
High regioselectivity in the heterocyclization of β-oxonitriles to 4-oxothiazolidines: X-ray structure proof
Markovi?, Rade,Baranac, Marija,D?ambaski, Zdravko,Stojanovi?, Milovan,Steel, Peter J.
, p. 7803 - 7810 (2007/10/03)
Base-catalyzed reactions of β-oxonitriles 1 with diethyl mercaptosuccinate favour heterocyclization to afford 2-alkylidene-4-oxothiazolidines 3, rather than 2-alkylidene-4-oxo-1,3-thiazinanes 4. The observed regioselectivity is based on spectroscopic and experimental evidence, including a single-crystal X-ray structure determination.
Regioselective synthesis and spectral characterization of ethyl (Z)- and (E)-2-alkylidene-4-oxothiazolidine-5-acetate derivatives. Solvent effects on the Z-E isomerization
Markovic, Rade,Baranac, Marija
, p. 893 - 903 (2007/10/03)
The title compounds containing an exocyclic double bond of exclusively the Z-configuration were prepared in anhydrous ethanol by the regio-selective base catalyzed reaction of diethyl 2-mercaptobutanedioate with nitrile precursors possessing an acidic α-hydrogen. The 1H NMR data indicating the presence of both geometrical isomers in primarily nonpolar media favoring the E-form are presented in terms of the solvent influence on intra- and intermolecular H-bonding and stereochemical outcome of the reaction.
