107171-75-5Relevant articles and documents
Ring-opening reactions of nonactivated aziridines catalyzed by tris(pentafluorophenyl)borane
Watson, Iain D. G.,Yudin, Andrei K.
, p. 5160 - 5167 (2003)
The ring-opening reactions of nonactivated aziridines with amine nucleophiles are efficiently catalyzed by tris(pentafluorophenyl)borane leading to derivatives of trans-1,2-diamines in high yields. A mechanistic investigation of the reaction suggests that in situ formed [(C6F5)3B(OH2)]· H2O catalyzes the opening through a Bronsted acid manifold.
Synthesis and enantioselectivity of optically active 1- and 3-substituted 4-phenyl-1,2,3,4-tetrahydroisoquinolin-4-ols and related compounds as norepinephrine potentiators
Kihara,Ikeuchi,Adachi,Nagao,Moritoki,Yamaguchi,Taira
, p. 1543 - 1546 (1995)
Optically active 1,2-dimethyl-4-phenyl-1,2,3,4-tetrahydroisoquinolin-4- ols (1R,4R-3a and 1S,4S-3b, 1S,4R-4a, and 1R,4S-4b) and 2-methyl-4-phenyl- 1,2,3,4-tetrahydroisoquinolines (4S-5a and 4R-5b) were prepared in order to examine the effects of the 1-, 3-, and 4-substituents of 2-methyl-4-phenyl- 1,2,3,4-tetrahydroisoquinolin-4-ol (PI-OH) (1) on the enantioselectivity for norepinephrine (NE) potentiating activity. The conformations and absolute configurations of 3-5 were determined from their 1H-NMR and circular dichroism (CD) spectra and by single-crystal X-ray diffractometric analysis. The NE potentiating activity of the optically active 3-5 and previously prepared 3-methyl derivatives (3R,4R-6a and 3S,4S-6b) of PI-OH were tested. The results show that compounds 3, 4, and 6 had high enantioselectivity for NE potentiation: the 4R series of the enantiomers exhibited activity but not the 4S-enantiomers. The activity of the 4-desoxy compound 5 also resided exclusively in the 4S-enantiomer. These findings suggest the presence of a specific receptor for NE uptake, and the enantiomers 3a, 4a, 5a, and 6a may be antagonistic at this NE uptake receptor.
Scope and limitations of montmorillonite K 10 catalysed opening of epoxide rings by amines
Chakraborti, Asit K.,Kondaskar, Atul,Rudrawar, Santosh
, p. 9085 - 9091 (2004)
Montmorillonite K 10 efficiently catalyses the opening of epoxide rings by amines in high yields with excellent regio- and diastereo-selectivities under solvent-free conditions at room temperature affording an improved process for synthesis of 2-amino alcohols. Reaction of cyclohexene oxide with aryl/alkyl amines leads to the formation of trans-2-aryl/alkylaminocyclohexanols. For unsymmetrical epoxides, the regioselectivity is controlled by the electronic and steric factors associated with the epoxide and the amine. Selective nucleophilic attack at the benzylic carbon of styrene oxide takes place with aromatic amines, whereas, aliphatic amines exhibit preferential nucleophilic attack at the terminal carbon. Aniline reacts selectively at the less hindered carbon of other unsymmetrical epoxides. The difference in the internal strain energy of the epoxide ring in cycloalkene oxides and alkene oxides led to selective nucleophilic opening of cyclohexene oxide by aniline in the presence of styrene oxide. Due to the chelation effect, selective activation of the epoxide ring in 3-phenoxy propylene oxide takes place in the presence of styrene oxide leading to preferential cleavage of the epoxide ring in 3-phenoxy propylene oxide by aniline.
Regioalternating Selectivity in the Metal Salt Catalyzed Aminolysis of Styrene Oxide
Chini, Marco,Crotti, Paolo,Macchia, Franco
, p. 5939 - 5942 (1991)
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An efficient protocol for regioselective ring opening of epoxides using sulfated tungstate: Application in synthesis of active pharmaceutical ingredients atenolol, propranolol and ranolazine
Pathare, Sagar P.,Akamanchi, Krishnacharya G.
, p. 6455 - 6459 (2013)
Sulfated tungstate was found to be a new and highly efficient catalyst for opening of epoxide rings by amines to give β-amino alcohols with high regioselectivity. Various advantages associated with this novel and environmental friendly protocol include solvent-free conditions, short reaction times, high product yields, simple workup procedure and easy recovery and reusability of the catalyst. This protocol has been applied for the synthesis of active pharmaceutical ingredients atenolol, propranolol and ranolazine.
Synthesis, characterization and catalytic application of Bi2S3 microspheres for Suzuki-Miyaura cross-coupling reaction and chemoselective ring opening of epoxides
Ghorbani-Choghamarani, Arash,Taherinia, Zahra
, (2020/11/20)
Bismuth sulfide (Bi2S3) prepared using L-cysteine, which served as both the sulfur source and the directing molecule for the formation of Bi2S3 as heterogeneous catalyst through solvothermal method. The prepared catalyst was examined by various techniques such as XRD, BET, FE-SEM, TEM, and TGA analysis. The results and analysis revealed that bismuth microspheres have better catalytic behavior for the preparation of biphenyl in water as a greenest solvent and for the ring opening of epoxides by nucleophiles including amines, alcohol, and thiol compared to pure Bi(NO3)3. 3H2O under solvent-free condition. Moreover, the novel catalyst could be recovered and reusedat least four times without loss of its catalytic activity.
Nickel-Catalyzed Regio- And Stereospecific C-H Coupling of Benzamides with Aziridines
Hirano, Koji,Miura, Masahiro,Xu, Shibo
, p. 5471 - 5475 (2021/07/26)
A nickel-catalyzed C-H coupling of 8-aminoquinoline-derived benzamides with aryl- and alkyl-substituted aziridines has been disclosed. The current strategy provides direct access to benzolactams by the C-H alkylation-intramolecular amidation cascade event with the concomitant removal of the aminoquinoline auxiliary. The regioselectivity of ring opening of aziridines can be controlled by the substituents. The reaction with chiral aziridines proceeds with inversion of configuration, thus suggesting an SN2-type nucleophilic ring-opening pathway.
M-Type SrFe12O19Ferrite: An Efficient Catalyst for the Synthesis of Amino Alcohols under Solvent-Free Conditions
Laayati, Mouhsine,Hasnaoui, Ali,Abdallah, Nayad,Oubaassine, Saadia,Fkhar, Lahcen,Mounkachi, Omar,El Houssame, Soufiane,Ait Ali, Mustapha,El Firdoussi, Larbi
, (2020/08/05)
Magnetically separable strontium hexaferrite SrFe12O19 was prepared using the chemical coprecipitation method, and the nanostructured material was characterized by X-ray diffraction, scanning electron microscopy (SEM), energy-dispersive spectrometry (EDS), and BET analysis. The SEM images showed the homogeneity of the chemical composition of SrFe12O19 and uniform distribution of size and morphology. The pore size of the nanomaterial and its specific area were determined by BET measurements. Strontium hexaferrite SrFe12O19 exhibited a strong magnetic field, which is highly suitable in the heterogeneous catalysis as it can be efficiently separated from the reaction. The magnetic nanocatalyst showed high activity and environmentally benign heterogeneous catalysts for the epoxide ring-opening with amines affording β-amino alcohols under solvent-free conditions. When unsymmetrical epoxides were treated in the presence of aromatics amines, the regioselectivity was influenced by the electronic and steric factors. Total regioselectivity was observed for the reactions performed with aliphatic amines. The magnetically SrFe12O19 nanocatalyst showed excellent recyclability with continuously good catalytic activities after four cycles.
