- Influence of the structure of polyfluorinated alcohols on Bronsted acidity/hydrogen-bond donor ability and consequences on the promoter effect
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The influence of substituents on the properties of tri-and hexafluorinated alcohols derived from 2,2,2-trifluoroethanol (TFE) and 1,1,1,3,3,3-hexafluoro-2- propanol (HFIP) was examined. Measurements of specific solvent-solute interactions revealed that H-
- Vuluga, Daniela,Legros, Julien,Crousse, Benoit,Slawin, Alexandra M. Z.,Laurence, Christian,Nicolet, Pierre,Bonnet-Delpon, Daniele
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- High-Pressure Promoted and Silica Gel Catalyzed Aminolysis of Epoxides with Glycine Esters
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A variety of epoxides are efficiently reacted with tert-butyl glycinates under high pressure conditions or by supporting on silica gel to afford the corresponding N-(β-hydroxyalkyl)glycine esters.
- Kotsuki, Hiyoshizo,Shimanouchi, Tomoyasu,Teraguchi, Masahiro,Kataoka, Masanori,Tatsukawa, Akira,Nishizawa, Hitoshi
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- Synthesis of new 3-phenoxypropan-2-ols with various heterocyclic substituents
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1-Phenoxy-3-piperidinopropan-2-ol, 1-(5-methyl-1,3-benzothiazol-2- ylsulfanyl)-3-phenoxypropan-2-ol, 1-(2-hydroxy-3-phenoxypropyl)azepan-2-one, 1,1′-(6-chloro-1,3-benzothiazol-2-ylimino)bis(3-phenoxypropan-2-ol), 1-(1,3-benzothiazol-2-ylsulfanyl)-3-phenox
- Mesropyan,Ambartsumyan,Avetisyan,Galstyan,Arutyunova
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- Synthesis and application of Cu(II) immobilized MCM-41 based solid Lewis acid catalyst for aminolysis reaction under solvent-free condition
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In this paper, a Cu(II) immobilized periodic mesoporous organosilica (PMOs) was synthesized and used as a reusable solid Lewis acid catalyst for the aminolysis of epoxides under solvent-free conditions. An amide-based ligand, L-propylsilyl (1) having a specific binding pocket was prepared and fabricated on mesoporous MCM-41 to produce mesoporous organosilica L-propylsilyl@MCM-41 (2). Further, it has been utilized for anchoring Cu(II) ions under controlled reaction conditions to yield solid Lewis acid catalyst Cu(II)-L-propylsilyl@MCM-41 (3). The synthesized catalyst 3 exhibits significantly higher catalytic activity for aminolysis compared to hitherto known solid Lewis acid catalysts. An extensive range of β-amino alcohols with high regio and stereoselectivity were prepared by using catalyst 3. The catalyst was recovered easily and reused eight times without any loss in its catalytic activity. Furthermore, the synthesis of clinically significant propranolol (β-blocker) from α- naphthyl glycidyl ether was attained successfully using catalyst 3 in a very decent yield.
- Chaudhary, Garima,Gupta, Neha,Singh, Amit Pratap
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- Fe(OH)3 nano solid material: An efficient catalyst for regioselective ring opening of aryloxy epoxide with amines under solvent free condition
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Iron hydroxide-Fe(OH)3and iron oxides (Fe3O4and Fe2O3) were successfully prepared and characterized. These materials were employed as efficient and environmentally benign heterogeneous catalysts for t
- Shah, Arpan K.,Prathap, K. Jeya,Kumar, Manish,Abdi, Sayed H.R.,Kureshy, Rukhsana I.,Khan, Noor-ul H.,Bajaj, Hari C.
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p. 442 - 450
(2017/02/05)
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- Solvent-free aminolysis of aliphatic and aryloxy epoxides with sulfated zirconia as solid acid catalyst
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Single-step and two-steps synthetic procedure for the synthesis of sulfated zirconia (SZ) was developed, which were calcined at 500, 600 and 700 °C and characterized by various physico-chemical methods such as PXRD, FTIR, surface area, microanalysis, NH3-TPD and DRIFT analysis. These SZ materials were then employed as solid acid catalysts for the aminolysis of different aliphatic/aromatic terminal, aryloxy and meso epoxides with aromatic and aliphatic amines under ambient conditions. Amongst the catalyst prepared, SZ-2-600 prepared in two-steps and 600 ° C calcined was found to be the most efficient catalyst to give p-amino alcohols in up to 98% yield and 7gt;99% regioselectivity. The SZ catalyst was successfully recycled and reused up to six catalytic runs with intact efficiency.
- Shah, Arpan K.,Kumar, Manish,Abdi, Sayed H.R.,Kureshy, Rukhsana I.,Khan, Noor-Ul H.,Bajaj, Hari C.
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p. 105 - 114
(2015/09/28)
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- Phenalenyl in a different role: Catalytic activation through the nonbonding molecular orbital
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We have demonstrated that the nonbonding molecular orbital (NBMO) of the phenalenyl (PLY) cation can be used as a Lewis acid catalyst for different organic transformations. Detailed computational and spectroscopic studies for the aminolysis reaction of ep
- Raha Roy, Sudipta,Nijamudheen,Pariyar, Anand,Ghosh, Anup,Vardhanapu, Pavan K.,Mandal, Prasun K.,Datta, Ayan,Mandal, Swadhin K.
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p. 4307 - 4319
(2015/02/19)
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- Efficient synthesis of β-amino alcohols by regioselective ring opening of epoxides with amines catalyzed by CuFe2O4 nanoparticles
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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.
- Baghbanian, Seyed Meysam,Farhang, Maryam
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p. 1033 - 1037
(2013/09/23)
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- Highly chemoselective addition of amines to epoxides in water
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(Chemical Equation Presented) Aminolysis of a variety of epoxides by aliphatic and aromatic amines in water, in the absence of any catalyst with high yields, is reported. β-Amino alcohols were formed under mild conditions with high selectivity and in excellent yields.
- Azizi, Najmodin,Saidi, Mohammad R.
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p. 3649 - 3651
(2007/10/03)
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- Process for the solid state synthesis of enantiopure B-aminoalcohols from racemic epoxides
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The invention relates to a process for the solid state synthesis of enantiopure β-aminoalcohols by preparing inclusion complexes of aryloxyepoxide with cyclodextrin by adding an epoxide in equimolar ratio in an organic solvent to an aqueous solution of cyclodextrin, reacting the cyclodextrin complex of aryloxyepoxide with a nucleophile in solid state by intimately grinding the mixture using a mortar and pestle, continuing the mixing till the starting epoxide disappeared on tic, removing excess amines under vacuum, extracting the β-aminoalcohols produced with a solvent with yields of more than 50% and enantioselectivity of upto 100%.
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- Opening of oxirane ring with N-nucleophiles under microwave irradiation
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Opening of oxirane ring under microwave irradiation with various N-nucleophiles in neutral, basic and acidic media is reported. Remarkable rate enhancements and dramatic reductions of reaction times have been observed with better yields.
- Gupta, Rajive,Paul, Satya,Gupta, Avinash K.,Kachroo, P. L.,Dandia, Anshu
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p. 281 - 283
(2007/10/03)
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- EFFECT OF THE MEDIUM ON THE RATE OF THE REACTION OF 1-PHENOXY-2,3-EPOXYPROPANE WITH PIPERIDINE AND N-METHYLPIPERIDINE
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The kinetics of the reaction of 1-phenoxy-2,3-epoxypropane with piperidine and N-methylpiperidine were studied in a series of aprotic solvents.The solvation effects, studied in terms of the Koppel-Palm equation, show that the determining factor in the var
- Kostenko, L. I.,Anikeev, A. V.,Koblik, I. V.,Popov, A. F.
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p. 760 - 762
(2007/10/02)
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- 3-Tertiary amino-1-aryloxy- or aryl-propanes and -propan -2-ols and some related compounds
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The synthesis and pharmacological activity of some 3 tertiary amino 1 aryloxy or 1 aryl, 1 thiophenoxy and 1 anilino propan 2 ols and propanes, particularly those derived from N phenylpiperazines are described. Effect of substituents (nature/position) on the phenyl ring, the phenoxy ring as well as alteration in the hydroxylic function vis a vis the structure activity relationships (SAR) are discussed. In general, the 1 aryloxy compounds have hypotensive activity this being more pronounced in those carrying an o substituent on the phenyl ring, while m and p substituted derivatives have their effect primarily on the CNS. Variations in the phenoxy moiety do not significantly alter the intrinsic activity. The 1 aryl compounds, on the other hand, have significant CNS activity, which is markedly affected by the substituents on the 1 aryl residue.
- Gupta,Mukerji,Chatterjee,Rastogi,Anand,Dube,Sur Jr.,Mukerji,Srimal
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p. 241 - 246
(2007/10/04)
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- 3-Aryloxy-2(4-loweralkyl-1-piperazinyl)propanols, their alkylethers, and use thereof
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Disclosed herein are compounds of the formula STR1 in which Ar is phenyl or 1-naphthyl; R1 is hydrogen or lower alkyl; and R2 and R3 together with the nitrogen atom to which they are joined form a hyterocyclic amine radical selected from the group consisting of 1-pyrrolidinyl, piperidino, morpholino and 4-(lower alkyl)-1-piperazinyl. The compounds are antidepressant agents and methods for their preparation and use also are disclosed.
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