7475-56-1Relevant 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.
AN IMPROVED SYNTHESIS OF α-CHLORODIPHENYLACETIC ACID
Maciel, J. B.,Gil, R. A. S. San,Neto, A. C.
, p. 76 - 77 (2007/10/03)
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Nucleophilic substitution in diphenylmethyl derivatives. II. Methanolysis of α substituents of diphenylacetic acid and its derivatives
Strazzolini, Paolo,Poiana, Marco,Verardo, Giancarlo,Giumanini, Angelo G.
, p. 283 - 289 (2007/10/02)
The nucleophilic displacement of α substituents of diphenylacetic acid and its methyl ester by MeOH under a variety of experimental conditions allowed us to establish that the reaction occurs rapidly in one of the following structural combinations: (a) carboxylate anion and a good leaving group; (b) carboxylic group and a less reactive leaving group; (c) methyl ester and a proton-activated, poor leaving group.The importance of internal hydrogen bonding (case b) was the governing factor in the outcome of the reaction of hydroxydiphenylacetic acid (3a) and its methyl ester 3b with acetyl chloride.The key intermediate in substitution at the α carbon is thought to be a carbocation stabilized both by the attached phenyl groups and, to a smaller extent, by the carboxyl group.