53673-51-1Relevant academic research and scientific papers
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.
Solvent-Directed Epoxide Opening with Primary Amines for the Synthesis of β-Amino Alcohols
Lizza, Joseph R.,Moura-Letts, Gustavo
, p. 1231 - 1242 (2017/03/11)
An efficient synthesis of β-amino alcohols from a variety of epoxides and primary unbranched amines in the absence of any catalyst in high yields and regioselectivities is reported. A variety of polar mixed solvent systems allow for the selective formation of secondary amino alcohols over tertiary amino alcohols. The reaction scope extends to a wide variety of aromatic and aliphatic substituted epoxides and primary amines bearing complex functionality.
Composition and reactivity of aminolysis products of phenyl glycidyl ether with benzylamine
Pal’chikov,Mykolenko, S. Yu.,Pugach,Zubkov
, p. 656 - 662 (2017/07/07)
Composition of aminolysis products of phenyl glycidyl ether with benzylamine in various conditions was studied. The ratio of 1-(benzylamino)-3-phenoxypropan-2-ol and 1,1'-(benzylazanediyl)bis(3-phenoxypropan-2-ol) does not considerably depend on the nature of the solvent and is basically determined by ratio of initial reagents. 2,6-Bis(phenoxymethyl)morpholine was obtained by dehydration of aminodiol in conditions of Mitsunobu reaction with subsequent reductive debenzylation.
Graphite oxide catalyzed synthesis of β-amino alcohols by ring-opening of epoxides
Mirza-Aghayan, Maryam,Alvandi, Farzaneh,Molaee Tavana, Mahdieh,Boukherroub, Rabah
, p. 70 - 79 (2017/03/14)
Graphite oxide as a heterogeneous and recyclable solid acid catalyzed a simple and efficient method for the synthesis of β-amino alcohols by ring opening of epoxides with amines. This method is effective with various aromatic and aliphatic amines under solvent-free conditions. The corresponding β-amino alcohols are obtained in high yields (56%-95%) and short reaction times (15-30 min) with high regio- and chemoselectivity under metal-free conditions.
Efficient synthesis of β-amino alcohols by regioselective ring opening of epoxides with amines catalyzed by CuFe2O4 nanoparticles
Baghbanian, Seyed Meysam,Farhang, Maryam
, p. 1033 - 1037 (2013/09/23)
A simple and efficient method has been developed for the synthesis of β-amino alcohols by regioselective ring opening of epoxides with amines in the presence of CuFe2O4 nanoparticles as a heterogeneous recyclable catalyst at room temperature in high yields.
Mg(ClO4)2, an efficient catalyst for synthesis of β-amino alcohols by ring opening of epoxides with amines under solvent-free conditions
Jafari, Abbas Ali,Moradgholi
experimental part, p. 594 - 602 (2011/04/15)
Commercially available magnesium perchlorate is reported as an extremely efficient catalyst for the ring-opening reaction of epoxide with various primary and secondary amines, especially diphenyl amine, under solvent-free conditions at room temperature.
A facile and efficient synthesis of β-amino alcohols using 2,2,2-trifluoroethanol as a metal-free and reusable medium
Khaksar, Samad,Heydari, Akbar,Tajbakhsh, Mahmood,Bijanzadeh, Hamid Reza
experimental part, p. 106 - 110 (2010/03/03)
Trifluoroethanol was used as a reusable catalyst and medium for the ring opening of epoxides using aliphatic and aromatic amines as nucleophile under mild conditions to give the corresponding β-amino alcohols in high yields and regioselectivity.
Quaternary ammonium bromide functionalized polyethylene glycol: A highly efficient and recyclable catalyst for selective synthesis of 5-aryl-2-oxazolidinones from carbon dioxide and aziridines under solvent-free conditions
Du, Ya,Wu, Ying,Liu, An-Hua,He, Liang-Nian
, p. 4709 - 4712 (2008/09/21)
(Chemical Equation Presented) A quaternary ammonium bromide covalently bound to polyethylene glycol (PEG, MW = 6000), i.e., PEG6000- (NBu3Br)2, was found to be an efficient and recyclable catalyst for the cycloaddition reaction of aziridines to CO2 under mild conditions without utilization of additional organic solvents or cocatalysts. As a result, 5-aryl-2-oxazolidinone was obtained in high yield with excellent regioselectivity. The catalyst worked well for a wide variety of 1-alkyl-2-arylaziridines. Besides, the catalyst could be recovered by centrifugation and reused without significant loss of catalytic activity and selectivity.
Microwave-enhanced sulphated zirconia and SZ/MCM-41 catalyzed regioselective synthesis of β-amino alcohols under solvent-free conditions
Negron-Silva, Guillermo,Hernandez-Reyes, C. Xochitl,Angeles-Beltran, Deyanira,Lomas-Romero, Leticia,Gonzalez-Zamora, Eduardo
, p. 977 - 985 (2008/09/18)
A solvent-free approach for the regioselective synthesis of β-amino alcohols in shorter reaction times and higher yields, compared to conventional heating is described. It involves microwave (MW) exposure of undiluted reactants in the presence of sulphated zirconia (SZ) or sulphated zirconia over MCM-41 (SZM) as catalyst. Both acid materials can be easily recovered and reused.
