87786-35-4Relevant articles and documents
Regioselective multicomponent sequential synthesis of hydantoins
Olimpieri, Francesca,Bellucci, Maria Cristina,Marcelli, Tommaso,Volonterio, Alessandro
, p. 9538 - 9555 (2013/01/16)
The development of new practical and green methods for the synthesis of small heterocycles is an attractive area of research due to the well-known potential of heterocyclic small molecule scaffolds in the drug discovery process. Herein we report a one-pot, three-component sequential procedure for the synthesis of diversely 1,3,5- and 1,3,5,5-substituted hydantoins, in high yields and very mild conditions, using readily accessible starting materials such as azides, iso(thio)cyanates and substituted α-halo-acetic carboxylic acids. This methodology is especially convenient for the synthesis of spiro-hydantoins, which are particularly interesting bioactive compounds in medicinal chemistry. The Royal Society of Chemistry 2012.
Enantioselectivity of the transfer of hydrogen atoms to acyclic prochiral carbon-centred radicals using chiral tin hydrides
Schwarzkopf, Kay,Blumenstein, Michael,Hayen, Ahlke,Metzger, Jürgen O.
, p. 177 - 181 (2007/10/03)
Racemic α-bromo esters 2 have been reduced via prochiral radicals 5 with low to moderate enantioselectivities using chiral tin hydrides 1 with a stereogenic tin atom containing chiral 2-[(1-dimethylaminoalkyl)phenyl] ligands. The tin hydrides 1 were mixtures of diastereomers. It could be shown that the minor diastereomer of tin hydrides 1a and 1b reacts with good enantioselectivity whereas the major diastereomer reacts almost unselectively. The observed enantioselectivities are also strongly influenced by steric effects of the substituents attached to the radical centre.
Electroreduction of Methyl 2-Bromo-2-phenylpropanoate on a Vitreous Carbon Electrode: meso- and DL-Dimethyl 2,3-Dimethyl-2,3-diphenylsuccinate
Luca, Carlo de,Inesi, Achille,Rampazzo, Liliana
, p. 1403 - 1408 (2007/10/02)
The electrochemical reduction of ethyl α-bromophenylacetate (1) and methyl 2-bromo-2-phenylpropanoate (5) in dry dimethylformamide on a vitreous carbon electrode has been studied.Dimeric products are formed as a consequence of controlled potential electrolysis of (1) and (5) on a reticulated vitreous carbon electrode.By this route, meso- and DL-diethyl 2,3-diphenylsuccinate and -dimethyl 2,3-dimethyl-2,3-diphenylsuccinate are obtained from ester (1) and (5), respectively.A triester is also obtained among the products.The spectral data (n.m.r., mass spectra) show the structure of this triester to be almost certainly MeO2CCMePhC6H4CMeCO2MeCMePhCO2Me (9).To explain the results, a mechanism is proposed, involving the formation of dimer (10) as an intermediate.