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.
An efficient synthesis of 2-amino alcohols by silica gel catalysed opening of epoxide rings by amines
Chakraborti, Asit K.,Rudrawar, Santosh,Kondaskar, Atul
, p. 1277 - 1280 (2004)
Silica gel (60-120 mesh) efficiently catalyses the opening of epoxide rings by amines at rt under solvent-free conditions providing an easy method for the synthesis of 2-amino alcohols. Aromatic and aliphatic amines react with cyclohexene oxide with exclu
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.
Stereospecific rearrangement of β-amino alcohols catalyzed by H 2SO4
Métro, Thomas-Xavier,Pardo, Domingo Gomez,Cossy, Janine
, p. 2888 - 2890 (2007)
Highly enantioselective rearrangement of β-amino alcohols was realized by using a catalytic amount of H2SO4. Georg Thieme Verlag Stuttgart.
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.
Solid lithium perchlorate as a powerful catalyst for the synthesis of β-aminoalcohols under solvent-free conditions
Azizi, Najmodin,Saidi, Mohammad R.
, p. 505 - 507 (2005)
Lithium perchlorate catalyzed the ring opening of epoxides with amines to provide the corresponding β-aminoalcohols in excellent yields with high regioselectivity. The reaction proceeds rapidly under mild and neutral conditions and worked well with primary, secondary, aliphatic, aromatic, and hindered amines in short times at room temperature, in the absence of solvent.
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.
Amine grafted Fe3O4 immobilized graphene oxide as a recyclable and effectual nanocomposite for the regioselective ring opening reaction
Gupta, Padmini,Garkoti, Charu,Shabir, Javaid,Surabhi,Sah, Digvijay,Mozumdar, Subho
, p. 4013 - 4028 (2021/06/25)
This work describes the synthesis of magnetic graphene oxide (MGO), where iron oxide (Fe3O4) nanoparticles were uniformly deposited over the sheets of the graphene oxide (GO). Further, the introduction of aminopropyltrimethoxysilane (APTMS) on the surface of MGO was successfully done and results in the formation of amine-functionalized magnetic graphene oxide (MGO–NH2). The synthesized heterogeneous magnetic nanocomposite was characterized by numerous physicochemical and morphological techniques such as powder X-ray diffraction, Fourier transform infrared, thermogravimetric analysis, transmission electron microscopy, vibrating sample magnetometer, scanning electron microscopy, CHN analyzer, and energy-dispersive X-ray analysis. The synthesized nanocomposite was proved to be an effectual catalyst in the nucleophilic ring opening reactions of styrene oxide with derivatives of amines under green solvent. The present catalyst displayed good catalytic activity, short reaction time, higher regioselectivity, excellent yields and could be reutilized up to seven catalytic rounds with no substantial loss in its activity. The excellent properties of the catalyst are due to the dual character of acidic groups (existence of carboxyl groups on the sheet edges) and basic groups (amine groups anchored on the surface of GO). On completion of the reaction, the prepared nanocomposite could be effortlessly recovered from the reaction mixture by utilizing an external magnet, owing to the ferromagnetic property of Fe3O4. Graphical Abstract: [Figure not available: see fulltext.].
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.
