- Mustard Carbonate Analogues as Sustainable Reagents for the Aminoalkylation of Phenols
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N,N-dialkyl ethylamine moiety can be found in numerous scaffolds of macromolecules, catalysts, and especially pharmaceuticals. Common synthetic procedures for its incorporation in a substrate relies on the use of a nitrogen mustard gas or on multistep syntheses featuring chlorine hazardous/toxic chemistry. Reported herein is a one-pot synthetic approach for the easy introduction of aminoalkyl chain into different phenolic substrates through dialkyl carbonate (β-aminocarbonate) chemistry. This new direct alcohol substitution avoids the use of chlorine chemistry, and it is efficient on numerous pharmacophore scaffolds with good to quantitative yield. The cytotoxicity via MTT of the β-aminocarbonate, key intermediate of this synthetic approach, was also evaluated and compared with its alcohol precursor.
- Annatelli, Mattia,Trapasso, Giacomo,Salaris, Claudio,Salata, Cristiano,Castellano, Sabrina,Aricò, Fabio
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supporting information
p. 3459 - 3464
(2021/05/24)
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- Urea-Zinc Chloride Eutectic Mixture-Mediated One-Pot Synthesis of Imidazoles: Efficient and Ecofriendly Access to Trifenagrel
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The low-melting mixture urea-ZnCl 2 was evaluated as a novel reaction medium for the synthesis of imidazoles. The reaction between a dicarbonyl compound, ammonium acetate, and an aromatic aldehyde is efficiently catalyzed by the eutectic solvent, yielding a wide variety of triaryl-1 H -imidazoles or 2-aryl-1 H -phenanthro[9,10- d ]imidazoles in good to excellent yields. In addition, the eutectic solvent was reused in five cycles without loss of its catalytic activity. This protocol was further explored for the synthesis of the drug trifenagrel, giving an excellent yield.
- Higuera, Natalia López,Pe?a-Solórzano, Diana,Ochoa-Puentes, Cristian
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p. 225 - 229
(2019/01/14)
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- Synthesis, cytotoxicity and topoisomerase inhibition properties of multifarious aminoalkylated indeno[1,2-c]isoquinolin-5,11-diones
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A number of mono- or diaminoalkylated indeno[1,2-c]isoquinolin-5,11-diones analogs of 1 were synthesized and evaluated for their DNA binding affinities, topoisomerase inhibition properties and antiproliferative activities against human cancer cell lines (
- Ahn, Gang,Schifano-Faux, Nadège,Goossens, Jean-Fran?ois,Baldeyrou, Brigitte,Couture, Axel,Grandclaudon, Pierre,Lansiaux, Amélie,Ryckebusch, Adina
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scheme or table
p. 2259 - 2263
(2011/05/15)
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- Room temperature synthesis of tri-, tetrasubstituted imidazoles and bis-analogues by mercaptopropylsilica (MPS) in aqueous methanol: application to the synthesis of the drug trifenagrel
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The heterogeneous solid catalyst, mercaptopropylsilica (MPS), has been prepared by a modified procedure in water and its structure confirmed by solid state carbon-13 CP-MAS NMR spectrum. This catalyst has been efficiently utilized for the synthesis of a w
- Mukhopadhyay, Chhanda,Tapaswi, Pradip Kumar,Drew, Michael G.B.
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scheme or table
p. 3944 - 3950
(2010/08/07)
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- Diphenyl-substituted heterocycles, processes for preparing them and their use as pharmaceutical compositions
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The invention relates to new diphenyl-substituted 5-ring heterocycles of general formula (I) wherein A, X and the groups R1, R2, R3, R4and R5are defined as in the claims, processes for preparing them
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- ortho-Directed Lithiation of (2-Methoxy)ethoxy- and (2-Dimethylamino)ethoxy-arenes
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ortho-Directed lithiation of a number of (2-methoxy)ethoxy- and (2-dimethylamino)ethoxy-arenes has been investigated.Lithiation of these compounds followed by treatment with various electrophiles afforded ortho-substituted products in moderate to excellent yields.Keywords-ortho-directed lithiation; (2-methoxy)ethoxyarene; (2-dimethylamino)ethoxyarene; regioselectivity
- Wada, Akimori,Kanatomo, Shoichi,Nagai, Sotoo
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p. 1016 - 1022
(2007/10/02)
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