3470-93-7Relevant academic research and scientific papers
Switchable synthesis of cyclic carbamates by carbon dioxide fixation at atmospheric pressure
Toda, Yasunori,Shishido, Minoru,Aoki, Tatsuya,Sukegawa, Kimiya,Suga, Hiroyuki
supporting information, p. 6672 - 6675 (2021/07/13)
The base-promoted switchable synthesis of five- and six-membered cyclic carbamates using atmospheric pressure carbon dioxide as the C1 source was developed. The chemoselectivity of products was simply controlled by changing bases and solvents. The reaction proceeds effectively under mild conditions, affording valuable cyclic carbamates. Experimental results and DFT studies revealed the reaction mechanism.
Synthesis and application of Cu(II) immobilized MCM-41 based solid Lewis acid catalyst for aminolysis reaction under solvent-free condition
Chaudhary, Garima,Gupta, Neha,Singh, Amit Pratap
, (2021/07/22)
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.
Stereocontrolled, Divergent, Al(lll)-Catalyzed Coupling of Chiral N-Aryl Epoxy Amines and CO2
Lee, Yuseop,Choi, Jonghoon,Kim, Hyunwoo
supporting information, p. 5036 - 5039 (2018/08/24)
A divergent coupling reaction was achieved between N-aryl epoxy amines and CO2. By using two different cocatalysts, tetrabutylammonium iodide (TBAI) or 4-dimethylaminopyridine (DMAP) together with an Al(III) Lewis acid, cyclic carbonates or oxazolidinones were selectively produced through two distinct reaction pathways, respectively. The proposed reaction mechanism was supported by the stereochemical determination of the products. A gram-scale production of Linezolid was successfully achieved.
Greener aminolysis of epoxides on BiCl3/SiO2
Mohsenzadeh, Farshid,Aghapoor, Kioumars,Darabi, Hossein Reza,Jalali, Mohammad Reza,Halvagar, Mohammad Reza
, p. 978 - 985 (2016/08/08)
The remarkable catalytic activity of BiCl3/SiO2 for the ring-opening of epoxides with aromatic and aliphatic amines under microwave and thermal heating was observed. This eco-friendly heterogeneous catalyst displayed high to excellent regioselectivity in the synthesis of β-amino alcohols under solvent-free conditions. High turnover frequency (TOF) values under microwave heating and excellent reusability of the catalyst may significantly contribute to applied chemistry.
Catalytic metallodendrimers grafted on mesoporous polymethacrylate beads for the regioselective synthesis of β-amino alcohols under solvent-free conditions
Tiwari, Richa,H. Daware, Sachdeo,Kale, Sandeep B.
, p. 42526 - 42535 (2015/05/20)
A new series of dendritic structures was grafted on epoxy activated mesoporous polymethacrylate beads (Sepabeads EB-EP-400). Grafting with the dendritic structures was followed by loading of metal termini to the chelating groups to form metallodendrimer-g
Fe(III) substituted Wells-Dawson type polyoxometalate: An efficient catalyst for ring opening of epoxides with aromatic amines
Aramesh,Yadollahi,Mirkhani
, p. 37 - 40 (2013/02/26)
Various β-aminoalcohols were prepared by the ring opening reaction of epoxides with aromatic amines in the presence of Fe(III) substituted Wells-Dawson type polyoxometalate, α2-[(n-C4H 9)4N]7P2/
Aminopropyl carbazole analogues as potent enhancers of neurogenesis
Yoon, Hye Jin,Kong, Sun-Young,Park, Min-Hye,Cho, Yongsung,Kim, Sung-Eun,Shin, Jae-Yeon,Jung, Sunghye,Lee, Jiyoun,Farhanullah,Kim, Hyun-Jung,Lee, Jeewoo
, p. 7165 - 7174 (2013/11/06)
Neural stem cells are multipotent and self-renewing cells that can differentiate into new neurons and hold great promise for treating various neurological disorders including multiple sclerosis, Parkinson's disease, and Alzheimer's disease. Small molecules that can trigger neurogenesis and neuroprotection are particularly useful not only because of their therapeutic implications but also because they can provide an invaluable tool to study the mechanisms of neurogenesis. In this report, we have developed and screened 25 aminopropyl carbazole derivatives that can enhance neurogenesis of cultured neural stem cells. Among these analogues, compound 9 demonstrated an excellent proneurogenic and neuroprotective activity with no apparent toxicity. We believe that compound 9 can serve as an excellent lead to develop various analogues and to study the underlying mechanisms of neurogenesis.
Efficient solvent-free aminolysis of epoxides under (C4H 12N2)2[BiCl6]Cl·H 2O catalysis
Lu, Hong-Fei,Sun, Lei-Lei,Le, Wen-Jun,Yang, Fei-Fei,Zhou, Jun-Tao,Gao, Yu-Hua
experimental part, p. 4267 - 4272 (2012/09/22)
An efficient and rapid procedure for ring opening of various epoxides with aromatic, aliphatic and heterocyclic amines is developed at room temperature under solvent-free conditions in the presence of (C4H 12N2)2[BiCl6]Cl·H 2O (1 mol %). This catalyst can be reused several times without losing of its activity.
Highly regioselective and efficient synthesis of aminoepoxides by ring closure of aminohalohydrins mediated by KF-Celite
Pace, Vittorio,Hoyos, Pilar,Sinisterra, José Vicente,Alcántara, Andrés R.,Holzer, Wolfgang
supporting information; experimental part, p. 1831 - 1834 (2011/09/16)
The regioselective synthesis of several aminoepoxides has been achieved without observing any trace of azetidinols, which are usually reported as the exclusive reaction products when aminohalohydrins are treated with bases. The use of the mild supported base KF-Celite in refluxing acetonitrile is crucial for modulating the excellent regioselectivity observed. Georg Thieme Verlag Stuttgart . New York.
First general route to substituted α-arylamino-α′ chloropropan-2-ones by oxidation of N-protected aminohalohydrins: The importance of disrupting hydrogen bond networks
Pace, Vittorio,Cabrera, Alvaro Cortes,Fernandez, Maria,Sinisterra, Jose V.,Alcantara, Andres R.
scheme or table, p. 3545 - 3555 (2010/12/19)
The presence of a network of intra- and intermolecular hydrogen bonds in β-arylamino alcohols, confirmed by both IR spectroscopy and computer modeling, inhibits their oxidation to the corresponding α-amino ketones. A straightforward protocol, including highly regioselective protection (as carbamates) and subsequent oxidation with Dess-Martin periodinane, affords near quantitative yields of the desired N-protected ketones, which upon mild treatment with iodotrimethylsilane leads to a series of differently functionalized α-arylamino-α′-chloro ketones. Georg Thieme Verlag Stuttgart.
