JOURNAL of the Tunisian Chemical Society

serving the Research, the Education and the Industry

Efficient synthesis of new chiral secondary amines derived from (-)-menthone

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New chiral imines 2a-i were prepared by condensation of (2S,5R)-(-)-2-isopropyl-5-methyl-cyclohexanone ((-)-menthone) 1 with primary amines. Diasiereoselective reduction of these imines with NaBH4 leads to the corresponding chiral secondary amines 3a-i with diastereomeric excess ranging from 46 to 98%.

R. El Abed, R. Touati, M. M'saddak, B. Ben Hassine

Menthone, Ketimines, Secondary amines, Diastereoselectivity

Pages 139-146

Synthesis and characterisation of some 1-aryl-5-morpholino Δ2-1,2,3-triazolines with biological potential

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The addition of arylazides to β-aminomethacrylic esters and nitrites led to 1-aryl-5-morpholino Δ2- 1,2,3-triazolines with good yields. The structure of these heterocycles with promising biological profile was determined by usual spectroscopic methods : IR, NMR and conforted by mass spectrometry.

M. Hamadouche, D. El Abed

Arylazides, Enamines, 1,3 Dipolar Cycloaddition, Triatolines, Spectroscopic Analysis

Pages 147-152

Isolation, for the first time, of a flavonoid glycoside and the (±)-catechin from the aerial parts of Ebenus pinnata

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From the aerial parts of Ebenus pinnata, a flavonol diglycoside and a mixture of two flavan-3-ol enantiomers were isolated for the first time and their structures elucidated as quercetin 3-O-α-L-rhamnosyl-(1 → 6)-O-β-D-glucopyranoside 1, and (±)-catechin 2. Their structures were established by ESIMS, EIMS, and 1D and 2D NMR spectral analysis.

H. Braham, H. Ben Jannet, L. Castedo, Z. Mighri

Ebenus pinnata, Leguminosae, (±)-catechin, favonol glycoside, rutin, NMR

Pages 153-160

Synthèse de phosphonopyrano et phosphonothiénopyrimidines

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The phosphonopyrano and thienopyrimidines are prepared by intermolecular cyclization reaction between the corresponding iminoethers derived from 2-aminophosphonopyranes and 2-aminophosphonothiophenes. The structure of all obtained products was determined on the basis of their IR and NRM data.

L. Ben Gaied, H. Zantour

phosphonoaminopyranes, phosphonoaminothiophenes, phosphonopyranopyrimidines, phosphonothieno-pyrimidines

Pages 161-171

Synthèse de carbamates N-sulfonylés-N-alkylés

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Triethylorthoformate and dimethoxymethane react with aroxy(alkoxy)sulfonylisocyanates 1a-g to give the corresponding N-alkylated carbamates 5a-g and 6a-g.

A. Akrmi, M. Beji, A. Baklouti

orthoformiate d'éthyle, diméthoxyméthane, aroxy(alcoxy)sulfonylisocyanate, carbamate

Pages 173-178

Synthèse et étude structurale de chrome tricarbonyl (dibenzo-18-couronne-5)

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Mono and bis-(tricarbonylchromium) compounds of dibenzo-18-Crown-5 have been synthesized from the reaction of the free crown ether (dibenzo-18-crown-5) with Cr(CO)6. The products have been characterized by spectroscopic means: 1H-NMR, 13C-NMR, IR, MS, by elemental analysis and by DSC. In addition the cis-isomer of dimetallic compound has been obtained as single crystals suitable for X-ray structure determination. The solid crystallizes in the orthorhombic system with cell parameters: a (Å) = 8.2378(2), b (Å) = 28.0352(4), c (Å) = 12.3424(3), Z=4 and space group Pnma.

A. Ben Hadj Amor, S. Top, J. Marrot, F. Meganem, G. Jaouen

bis-(tricarbonyl chromium) dibenzo-18-crown-5, synthesis, structural resolution

Pages 179-187

Préparation et structure cristalline du 1,4,7,10,13-benzopentaoxacyclopentadecin-2,3,5,6,8,9,11,12-octahydro-15,16-dinitro

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The synthesis of 1,4,7,10,13- BenzopentaoxacycIopentadecin-2,3,5,6,8,9,11,12-octahydro-15,16-dinitro is achieved by the nitration of 1,4,7,10,13-benzopentaoxacyclodecin-2,3,5,6,8,9,11,12-octahydro. This compound is characterized by spectroscopic technics, IR, UV, 1H-NMR, 13C-NMR, mass spectrometry and by XR diffraction. A monocrystal from the product was selected and its crystal structure solved. The solid crystallizes in the monoclinic system with space group P21/n and a := 11,7443 (3) ; b = 8,5135 (3) ; c = 17,4845(5) Å ; β = 108,324 (1 )° and Z = 4. The cavities of the macrocycle are rigidified by five intramolecular hydrogen bonds, whereas six hydrogen bonds between a molecule and three near neighbors ensure crystal cohesion.

A. Ouerghi, A. Ben Hadj Amor, J. Marrot, F. Meganem

Dinitrobenzo-15-crown-5, crystal structure of C14H18N2O9

Pages 189-194

Structure cristalline du N2-phényl-N2-tosyl-acéthydrazide C15H16N2O3S

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The ethyl N1-phenyl acethydrazonate reacts in pyridin with tosyl chloride to give after hydrolysis the N2-phenyl-N2-Tosyl-acethydrazide. The X-ray crystal structure of this compound has been determined and confirms the proposed structure. The C15H16N2O3S crystallizes in the monoclinic system with space group P21/c, the unit cell dimensions are: a .= 9.284(1), b = 18144(1), c = 17.893(1) Å, β = 91.822(2)° with z = 4 and px = 1.292 The average structure was refined at R = 0.0605 and Rw = 0.1822. Examination of the structure shows isolated dimers of C30H32N4O6S2 parallel to the [100] direction : the molecules are connected through intermolecular hydrogen bonds.

S. Chaabouni, M. Kossentini, A. Ben Salah, M. Salem

N2-phenyl-N2-Tosyl-acethydrazide, Crystal structure

Pages 195-202

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