87786-35-4Relevant academic research and scientific papers
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.
Indium-mediated Reformatsky-Claisen rearrangement
Ishihara, Jun,Watanabe, Yuki,Koyama, Noriko,Nishino, Yukihiro,Takahashi, Keisuke,Hatakeyama, Susumi
body text, p. 3659 - 3667 (2011/06/21)
A new variant of the Reformatsky-Claisen rearrangement is described. The reaction of substituted allyl α-bromoacetates with indium and indium(III) chloride under ultrasonication provides a general entry into the functionalized synthon.
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.
Acide 2-fluoro-2-phenyl propanoique: preparation et utilisation comme agent chiral de derivation
Hamman, S.
, p. 225 - 232 (2007/10/02)
The enantiomers of 2-fluoro-2-phenyl propanoic acid have been separated and their absolute configurations determined: the specific rotation of the acid with an R configuration is 20D= -28.5 deg (c=1.5, ethanol).This acid has been
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.
