0000000000138940
AUTHOR
El Mestafa El Hadrami
showing 11 related works from this author
Experimental and theoretical DFT study of the reaction of 3-amino-1,2-diols with dichloromethane and paraformaldehyde
2004
Abstract The reactions of 3-phenyl-3-methylamino-1,2-propanediol 1a and 3-[(tert-butyldimethylsilyl)oxy]-1-methylamino-1-phenyl-2-propanol 1b with (CH2O)n and CH2Cl2 are appropriate procedures for the preparation of 1,3-oxazines or 1,3-oxazolidines under proper selection of kinetic or thermodynamic reaction conditions. The reaction of 1b with (CH2O)n or CH2Cl2, affords the oxazolidine 2b under kinetic conditions and then this compound can be slowly converted into 5-[(tert-butyldimethylsilyl)oxy]-3-methyl-4-phenyl-3,4,5,6-tetrahydro-2H-1,3-oxazine 3b under thermodynamic control. The mechanism proposed for this transformation and the effect of polar solvents on the acceleration of the reactio…
Supramolecular arrangements of novel clickable 4-substituted 3,6-bis(2′-pyridyl)pyridazine molecules
2020
Abstract The clickable reaction between the starting 3,6-bis(2′-pyridyl)-1,2,4,5-tetrazine (bptz) with a series of terminal alkynes-containing functional biomolecules [prop-2-yn-1-ol, 4-(prop-2′-yn-1′-yl)morpholine and D-galactose] by means of an inverse electron demand Diels-Alder pathway has been studied and four new 4-substituted 3,6-bis(2′-pyridyl)pyridazine derivatives (4-Rdppn) were isolated, namely 4-(hydroxymethyl)-3,6-di(pyridin-2-yl)pyridazine (1), 4-((prop-2-yn-1-yloxy)methyl)-3,6-di(pyridin-2-yl)pyridazine (2) obtained by post-etherification reaction of 1, 4-(morpholinemethyl)-(3,6-dipyridin-2-yl)pyridazine monohydrate (3) and 3,6-di(pyridin-2-yl)-4-((2,2,7,7-tetramethyltetrahyd…
Synthesis and characterization of new 1,4 and 1,5-disubstituted glucopyranosyl 1,2,3-triazole by 1,3-dipolar cycloaddition
2009
Abstract A series of 1,4 and 1,5-disubstituted 1-(β- d -glucopyranosyl)-1,2,3-triazoles has been prepared in an efficient manner with excellent yields using the intermolecular 1,3-dipolar cycloaddition of 1-azido-2,3,4,6-tetra-O-acetyl-β- d -glucopyranose 2 to a variety of substituted alkynes phenylacethylene 3, propargyl alcohol 4, 2-butyn-1,4-diol, 5, 3-propargylbenzimidazole 6 and propargylpyrazole 7 in toluene. The reaction takes place with the formation of both 4- and 5-regioisomers.
Synthesis, characterization and X-ray structure of glycosyl-1,2-isoxazoles and glycosyl-1,2-isoxazolines prepared via 1,3-dipolar cycloaddition
2013
Abstract A convenient preparative method of a series of glycosyl-1,2-isoxazoles ( 6–11 ) and glycosyl-1,2-isoxazolines ( 15–20 ) by a simple and efficient 1,3-dipolar cycloaddition of a series of aryl nitrile oxide, generated in situ from aryl oximes ( 4–5 ), with a variety of O -propargyl glycosyles ( 1 – 3 ) or O -allyl glycosyles ( 12–14 ) respectively, is reported. The carbohydrate-containing 1,2-isoxazoles and 1,2-isoxazolines compounds were isolated in excellent yields (81–91%) and they were fully characterized by 1 H, 13 C NMR and mass spectrometry. The relative stereochemistry of the glycosyl-1,2-isoxazole 10 was confirmed by single crystal X-ray analysis. The molecular structure of…
Reactivity difference between diphosgene and phosgene in reaction with (2,3-anti)-3-amino-1,2-diols
2006
In reactions of (2,3-anti)-3-amino-1,2-diols with diphosgene and phosgene and their conversion into 1,3-oxazolidin-2-ones, some differences in the stereochemistry of the reactions have been found with these two reagents. The reactions with phosgene afforded the expected cis-oxazolidinones, and in the reaction with diphosgene under the same reaction conditions, the trans-oxazolidinones were also obtained.
Experimental and DFT study of the conversion of ephedrine derivatives into oxazolidinones. Double SN2 mechanism against SN1 mechanism
2010
Sulfonation of the N-Boc derivatives of 1,2-aminoalcohols, such as ephedrine, pseudoephedrine, norephedrine, norpseudoephedrine, thiomicamine, and chloramphenicol yields a mixture of the corresponding oxazolidinones with inversion (erythro derivatives) and/or retention of configuration (threo derivatives)at C5. We suggest a competition between two mechanisms: an intramolecular SN2 process initiated by attack of the carbonyl oxygen of the Boc group to the benzylic carbon and the other one through a double SN2 process. In the erythro derivatives the first mechanism is predominant, while in the threo derivatives both mechanisms have similar energy. This hypothesis is supported by theoretical c…
Novel examples of the N-methyl effect on cyclisations of N-Boc derivatives of amino alcohols. A theoretical study
2004
New examples of the N-methyl effect on the cyclisation of N-tert-butoxycarbonyl derivatives of amino alcohols are reported. Ab initio studies for the displacement step with formation of the five-membered heterocycle indicate that the increase of the nucleophile character of the carbonyl oxygen of the carbamate group with the N-methyl substitution is responsible for the acceleration of the cyclisation step.
CCDC 1977986: Experimental Crystal Structure Determination
2020
Related Article: Mouad Filali, El Mestafa El Hadrami, Rosaria Bruno, Giovanni De Munno, Abdeslem Bentama, Miguel Julve, Salah-Eddine Stiriba|2020|J.Mol.Struct.|1217|128420|doi:10.1016/j.molstruc.2020.128420
CCDC 923498: Experimental Crystal Structure Determination
2013
Related Article: Issam Gaamoussi, Ismail Fichtali, Abdeslem Ben Tama, El Mestafa El Hadrami, Donatella Armentano, Giovani De Munno, Miguel Julve, Salah-Eddine Stiriba|2013|J.Mol.Struct.|1048|130|doi:10.1016/j.molstruc.2013.05.043
CCDC 1977987: Experimental Crystal Structure Determination
2020
Related Article: Mouad Filali, El Mestafa El Hadrami, Rosaria Bruno, Giovanni De Munno, Abdeslem Bentama, Miguel Julve, Salah-Eddine Stiriba|2020|J.Mol.Struct.|1217|128420|doi:10.1016/j.molstruc.2020.128420
CCDC 1977985: Experimental Crystal Structure Determination
2020
Related Article: Mouad Filali, El Mestafa El Hadrami, Rosaria Bruno, Giovanni De Munno, Abdeslem Bentama, Miguel Julve, Salah-Eddine Stiriba|2020|J.Mol.Struct.|1217|128420|doi:10.1016/j.molstruc.2020.128420