351345-59-0Relevant articles and documents
Application of optically active aminonaphthols as NMR solvating agents for chiral discrimination of mandelic acid
Chaudhary, Anju R.,Yadav, Priyanka,Bedekar, Ashutosh V.
, p. 767 - 774 (2014/06/09)
A series of optically active aminonaphthol derivatives were prepared and screened as chiral solvating agents to discriminate the CαH of racemic mandelic acid by 1H NMR analysis. An effort was made to establish a correlation of the structure of aminonaphthol derivatives and the selectivity in this non-covalent interaction. A linear relationship between the experimental and calculated enantiomeric purity was established by indicating the potential use of the system to determine the ee for the samples of mandelic acid of unknown enantiomeric purity.
Bioactivity of a family of chiral nonracemic aminobenzylnaphthols towards candida albicans
Capozzi, Maria Annunziata M.,Cardellicchio, Cosimo,Magaletti, Angela,Bevilacqua, Antonio,Perricone, Marianne,Corbo, Maria Rosaria
, p. 5219 - 5230 (2014/05/20)
Chiral nonracemic aminobenzylnaphthols were obtained by a Betti multicomponent reaction between 2-naphthol, aryl aldehydes and enantiopure arylethylamine. Moreover, some new aminobenzylnaphthols were synthesized by a similar reaction between 2-naphthol, aryl aldehydes and prolinol. These aminobenzylnaphthols, synthesized from different components and thus having different structural features, were tested as anti-yeast agents inhibiting Candida albicans. The effect towards the test strain was studied with a microdilution approach and three different concentrations (150, 300 and 450 μg/mL) were tested. The best results were found for the aminobenzylnaphthols obtained from 1-naphthylethylamine and from natural prolinol. The use of the two-way ANOVA highlighted the better performances of the prolinol derivative among the differently structured aminobenzylnaphthols that were screened. The activity towards C. albicans of this prolinol derivative resulted to be interesting and could represent a promising alternative to overcome the problem of the strains resistant to the traditional antifungals.
Investigation on the weak interactions assembling the crystal structures of Betti bases
Cardellicchio, Cosimo,Capozzi, Maria Annunziata M.,Alvarez-Larena, Angel,Piniella, Joan F.,Capitelli, Francesco
experimental part, p. 3972 - 3981 (2012/07/28)
The crystal structures of (S, S)-aminobenzylnaphthols, easily produced by a chromatography-free highly stereoselective Betti reaction, were investigated by means of single crystal X-ray diffraction analysis, and the main intra- and intermolecular interactions were described. The presence of a strong intramolecular hydrogen bond was confirmed, whereas the whole crystal building was found to be due mainly to other bondings, such as CH...O and CH...π interactions. As far as the last interactions were concerned, we observed many short distances from one hydrogen atom to an aryl plane, together with the appropriate geometric requirements for the assemblies. The observations suggest that these interactions can play a relevant role in the crystal building. The absence of similar short distance CH...π interactions in the crystal of a diastereomeric (R, S)-aminobenzylnaphthol could be a suggestion of the preferential crystallisation of the (S, S)-stereoisomer and, consequently, its prevalence as a product of the Betti reaction.
Application of 1-(α-aminobenzyl)-2-naphthols as air-stable ligands for pd-catalyzed Mizoroki-Heck coupling reaction
Chaudhary, Anju R.,Bedekar, Ashutosh V.
experimental part, p. 1778 - 1785 (2012/04/10)
Air-stable, easily accessible Mannich bases, 1-(α-aminobenzyl)-2- naphthols, are used as ligands in palladium-catalyzed Mizoroki-Heck reaction on a variety of substrates. High turnover numbers are observed for both the reactions with aryl bromides and iodides, while aryl chlorides are inert. Copyright Taylor & Francis Group, LLC.
Structural influence of chiral tertiary aminonaphthol ligands on the asymmetric phenyl transfer to aromatic aldehydes
Wei, Hui,Yin, Lu,Luo, Haibin,Li, Xingshu,Chan, Albert S. C.
experimental part, p. 222 - 227 (2012/03/27)
A series of chiral tertiary aminonaphthol ligands were prepared from 2-naphthol, (S)-1-phenylethylamine, and aldehydes with diverse substituted groups. The results of asymmetric phenyl transfer to aromatic aldehydes catalyzed by these chiral ligands indicated that enantioselectivities were greatly influenced by the electronic and steric effects of the ligands. Copyright
The application of chiral aminonaphthols in the enantioselective addition of diethylzinc to aryl aldehydes
Liu, Da-Xue,Zhang, Li-Cheng,Wang, Quan,Da, Chao-Shan,Xin, Zhuo-Qun,Wang, Rui,Choi, Michael C. K.,Chan, Albert S. C.
, p. 2733 - 2735 (2007/10/03)
(Equation presented) Optically active aminonaphthol 3 obtained by condensation of 2-naphthol, benzaldehyde, and (S)-methylbenzylamine followed by N-methylation was found to catalyze the enantioselective ethylation of aryl aldehydes to secondary alcohols w
Mechanism and Diastereoselectivity of the Reactions Between Naphthols and Imines
Boga, Carla,Martino, Emanuela Di,Forlandi, Luciano,Torri, Federica
, p. 219 - 235 (2007/10/03)
The reactions between β-naphthol and imines (both aliphatic and homo- or heterocyclic in the amine moiety) produce N-substituted-1-(α-aminobenzyl)-2-naphthol. The reaction between β-naphthol and (S)-N-benzylidene-1-phenylethanamine produces both diastereomers in a ratio which depends on the reaction times and temperature. Independent experiments show that there is an equilibration of the two diastereomers. The mechanism of the title reactions involves a proton donor-acceptor interaction which is responsible also for the observed equilibration of diastereomers.
