- Nickel Boride Catalyzed Reductions of Nitro Compounds and Azides: Nanocellulose-Supported Catalysts in Tandem Reactions
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Nickel boride catalyst prepared in situ from NiCl2 and sodium borohydride allowed, in the presence of an aqueous solution of TEMPO-oxidized nanocellulose (0.01 wt%), the reduction of a wide range of nitroarenes and aliphatic nitro compounds. Here we describe how the modified nanocellulose has a stabilizing effect on the catalyst that enables low loading of the nickel salt pre-catalyst. Ni-B prepared in situ from a methanolic solution was also used to develop a greener and facile reduction of organic azides, offering a substantially lowered catalyst loading with respect to reported methods in the literature. Both aromatic and aliphatic azides were reduced, and the protocol is compatible with a one-pot Boc-protection of the obtained amine yielding the corresponding carbamates. Finally, bacterial crystalline nanocellulose was chosen as a support for the Ni-B catalyst to allow an easy recovery step of the catalyst and its recyclability for new reduction cycles.
- Proietti, Giampiero,Prathap, Kaniraj Jeya,Ye, Xinchen,Olsson, Richard T.,Dinér, Peter
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p. 133 - 146
(2021/11/04)
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- A new way to do an old reaction: highly efficient reduction of organic azides by sodium iodide in the presence of acidic ion exchange resin
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Organic azides are readily reduced to the corresponding amines by treatment with sodium iodide in the presence of acidic ion exchange resin. The process, optimal when performed at 40 °C and 200 mbar pressure on a rotatory evaporator, is extremely efficient, clean, and tolerant of a variety of functional groups.
- Suthagar, Kajitha,Fairbanks, Antony J.
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supporting information
p. 713 - 715
(2017/01/13)
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- Iodine monochloride (ICl) as a highly efficient, green oxidant for the oxidation of alcohols to corresponding carbonyl compounds
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Iodine monochloride (ICl) was discovered to be a highly efficient, green oxidant, which can oxidize aldose hemiacetals, diarylmethanols, arylalkylmethanols, anddialkylmethanols to the corresponding aldose lactones, diarylmethanones, arylalkylmethanones, and dialkylmethanones, respectively, in high yields. ICl as a green, metal-free oxidant is characterized by mild reaction condition, short reaction time, good yield, and broad scope.
- Wei, Peng,Zhang, Datong,Gao, Zhigang,Cai, Wenqing,Xu, Weiren,Tang, Lida,Zhao, Guilong
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supporting information
p. 1457 - 1470
(2015/05/20)
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- A straightforward and versatile approach to the synthesis of 1,4,5-trisubstituted 1,2,3-triazoles from alkyl halides via a one-pot, three-component reaction
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The preparation of 1,4,5-trisubstituted 1,2,3-triazoles by the coupling of three components (alkyl halides, sodium azide, and active ketones) through an azide-enolate [3+2] cycloaddition (Dimroth cycloaddition) has been developed for the first time. A wide variety of halides (including chlorides, bromides, and iodides as well as primary and secondary derivatives) have demonstrated the versatility of this method, which is based on a one-pot system under mild reaction conditions.
- González-Calderón, Davir,Aguirre-De Paz, José G.,González-González, Carlos A.,Fuentes-Benítes, Aydeé,González-Romero, Carlos
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p. 1713 - 1715
(2015/03/14)
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- Linear poly(amide triazole)s derived from d -glucose
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The click reaction between azides and alkynes is been increasingly employed in the preparation of polymers. In this article, we describe the synthesis and click polyaddition reaction of a new A-B-type amide monomer - prepared from d-glucose as renewable r
- Molina-Pinilla, Inmaculada,Bueno-Martinez, Manuel,Hakkou, Khalid,Galbis, Juan A.
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p. 629 - 638
(2014/02/14)
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- Click chemistry inspired highly facile synthesis of triazolyl ethisterone glycoconjugates
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Numerous deoxy-azido sugars 3 were prepared by the reaction of tosyl/bromo sugars with NaN3 in dry DMF under heating condition. The 1,3-dipolar cycloaddition of deoxy-azido sugars 3 with ethisterone 4 to afford regioselective triazole-linked ethisterone glycoconjugates 5 was investigated in the presence of CuI and DIPEA in dichloromethane or CuSO4· 5H2O and sodium ascorbate in aqueous medium. All the developed compounds were characterized by spectroscopic analysis (IR, 1H & 13C NMR, and MS spectra). Structure of triazolyl ethisterone glycoconjugate 5a has been further confirmed by its Single Crystal X-ray analysis.
- Kumar, Dhananjay,Mishra, Kunj B.,Mishra, Bhuwan B.,Mondal, Saheli,Tiwari, Vinod K.
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supporting information
p. 71 - 79
(2014/01/17)
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- Evaluation of potential Myt1 kinase inhibitors by TR-FRET based binding assay
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In the human cell cycle, the Myt1 kinase is a crucial regulator of the G2/M transition. Because this membrane-associated kinase is hard to obtain and assay, there is a distinct lack of data so far. Here we report the derivatization of a glycoglycerolipid which was shown previously to be active in a Myt1 activity assay. These compounds were tested in a binding assay together with a set of common kinase inhibitors against a full-length Myt1 expressed in a human cell line. Dasatinib exhibited nanomolar affinity whereas broad coverage inhibitors such as sunitinib and staurosporine derivatives did not show any effect. We also carried out docking studies for the most potent compounds allowing further insights into the inhibitor interaction of this kinase. The glycoglycerolipids showed no significant effects in the binding assay, endorsing the idea of a mechanism of action distant from the active site.
- Rohe, Alexander,Goellner, Christiane,Wichapong, Kanin,Erdmann, Frank,Al-Mazaideh, Ghassab M.A.,Sippl, Wolfgang,Schmidt, Matthias
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- Skeletal rearrangement of seven-membered iminosugars: Synthesis of (-)-adenophorine, (-)-1-epi-adenophorine and derivatives and evaluation as glycosidase inhibitors
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The mirror image of natural product (+)-adenophorine along with its 1-epi-, 1-homo-analogs and other derivatives have been synthesized and evaluated as glycosidase inhibitors. The synthetic strategy is based on the skeletal rearrangement of tetrahydroxylated C-alkyl azepanes obtained via a Staudinger/azaWittig/alkylation sequence starting from a sugar-derived azidolactol. Several organometallic species have been investigated for the alkylation step including organomagnesium, organolithium, organozinc, organoaluminum and organocerium reagents. While diallylzinc proved to be the most efficient to introduce an allyl substituent, disappointing results were obtained with the other organometallic species leading either to lower yields or no reaction. Enzymatic assays indicate that (-)-adenophorine is a moderate α-l-fucosidase inhibitor.
- Mondon, Martine,Lecornué, Frédéric,Guillard, Jér?me,Nakagawa, Shinpei,Kato, Atsushi,Blériot, Yves
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p. 4803 - 4812
(2013/08/23)
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- Synthesis and glycosidase inhibitory profiles of functionalised morpholines and oxazepanes
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In this work libraries of morpholines and oxazepanes have been prepared via the reductive amination reaction between dialdehydes, derived from carbohydrates, and a range of amines. In this way, functionalised morpholines and oxazepanes have been prepared
- Burland, Peter A.,Osborn, Helen M.I.,Turkson, Andrea
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p. 5679 - 5692
(2011/10/31)
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- Microwave irradiation as an effective means of synthesizing uninfstituted N-linked 1,2,3-triazoles from vinyl acetate and azides
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N-Linked 1,2,3-triazoles have been prepared by a reaction of azides with vinyl acetate under microwave irradiation. Additionally, a microwave-assisted, two-step, one-pot procedure from halides involving azideinfstitution in diethyl ether, followed by -reaction with vinyl acetate, has effectively been employed. Georg Thieme Verlag Stuttgart - New York.
- Hansen, Signe Grann,Jensen, Henrik Helligs?
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experimental part
p. 3275 - 3278
(2010/03/03)
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- First total synthesis of 1,2-dipalmitoyl-3-(N-palmitoyl-6′-amino-6′-deoxy-α-d-glucosyl)-sn-glycerol-a glycoglycerolipid of a marine alga with a high inhibitor activity against human Myt1-kinase
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The first total synthesis of 1,2-dipalmitoyl-3-(N-palmitoyl-6′-amino-6′-deoxy-α-d-glucosyl)-sn-glycerol, a glycoglycerolipid isolated from a marine alga extract, is described. Starting from α-methylglucopyranoside the multistep strategy allows the stereoselective synthesis of the final compound using various protective group procedures as well as derivatization of partial molecule domains. The latter offers the development of lead structures for inhibitors of human Myt1-kinase.
- Goellner, Christiane,Philipp, Claudia,Dobner, Bodo,Sippl, Wolfgang,Schmidt, Matthias
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scheme or table
p. 1628 - 1631
(2009/12/09)
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- Synthesis of a trisaccharide library by using a phenylsulfonate traceless linker on synphase crowns
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44 members are in the trisaccharide library synthesized by the method described here. Six differently protected glucoside building blocks were sulfonylated with 1, coupled to the solid support 2 (a crown compound) by Pd0-catalyzed carbonylative
- Takahashi, Takashi,Inoue, Hitoshi,Yamamura, Yuichi,Doi, Takayuki
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p. 3230 - 3233
(2007/10/03)
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- Synthesis of biomimetic analogs of neomycin B: Potential inhibitors of the HIV RNA Rev response element
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The aminoglycosidic antibiotic, neomycin B, is an inhibitor of the binding of Rev to RRE. This paper reports on the synthesis of analogs of neomycin B as potential anti-HIV compounds designed to function as inhibitors of Rev/RRE binding.
- Nishizono, Naozumi,Nair, Vasu
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p. 283 - 295
(2007/10/03)
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