Thouraya Barhoumi-Slimi

• PhD
• Professor (Full) at University of Carthage

Linseed oil-based composite films were prepared with cinnamaldehyde (Cin) using a modified clay (organoclay) through in situ polymerization, which is the result of the interaction between Cin and organoclay. The incorporation of organoclay reduces the polymer chain’s mobility and, therefore, increases the thermal stability of the composite films. I...

New α,β-unsaturated-2,5-disubstituted-1,3,4-Oxadiazoles (4a–j) and (10a–d) have been prepared in good to excellent yields starting from β-chlorovinyl aldehydes and hydrazide. The synthesized oxadiazoles were fully characterized by (¹H, ¹³C) NMR, IR and HRM Sspectroscopic techniques. The in vivo antitumor activity of 4b, 4c, 4g, 4d, and 10c was eval...

Orthogonal chemistry is a valuable tool in the preparation of complex molecules as heteroglycoclusters. Unfortunately, selective heteroconjugation of multifunctional starting materials remains a usually challenging problem to overcome. Herein, we report the first report on harnessing N‐alkylation of N‐acylhydrazone as a key step in the orthogonal s...

A one-pot synthesis of new variously substituted γ-chloro-γ,β-allylic carbamates have been carried out starting from β-chloro-α,β-unsaturated aldehydes. The new carbamates and the corresponding intermediates, the γ-chloro-γ,β-allylic alcohols, were fully characterized by (¹H and ¹³C) NMR, IR and HRMS spectroscopic techniques. The crystal structures...

A convenient synthesis of a series of new β-fluoroalkoxyvinyl aldehydes and their corresponding alcohols from β-chloro-α,β-unsaturated aldehydes was developed. The etherification reaction and the carbonyl reduction were successfully achieved, affording the desired products in good yields. The mechanism of the nucleophilic vinylic substitution react...

A series of six new p-tert-butylcalix [4]arene-1,3-N,N′-diacylhydrazone derivatives 1–6 have been synthesized starting from β-chloro-α,β-unsaturated aldehydes and p-tert-butylcalix [4]arene hydrazide. They were characterized by IR, ( ¹ H, ¹³ C, ¹⁹ F) NMR and HRMS. In addition of the E/Z isomers around the C[dbnd]C bond of the starting aldehydes, th...

The synthesis of new substituted arylphosphoramidates is performed in two steps through phosphorylation of the corresponding alcohols followed by aminolysis. The formation of the desired phosphoramidates depends on the subsequent addition of the two alcohols with the amine being added at the last step. The products were obtained in 58–95% yields. T...

The reaction of tin tetrachloride with a series of variously substituted α-hydroxyphosphonates (L) in anhydrous dichloromethane produces new octahedral tin complexes of the type [SnCl4L2]. These adducts were characterized by multinuclear (¹H, ¹³C, ³¹P and ¹¹⁹Sn) NMR, IR spectroscopy, and elemental analysis. The NMR data show that these complexes ex...

A series of new α-hydroxyphosphonate (5–14) have been synthesized in high yields by reaction of β-chloro-α,β-unsaturated aldehydes (1–4) and trialkyl phosphite in the presence of chlorotrimethylsilane at room temperature under solvent-free conditions. In addition, compounds (5–14) were reacted with acetic anhydride in DBU to give the new α-acetoxyp...

The Diels–Alder reactions of three β-chloro-α,β-unsaturated carbonyl compounds 1–3 with different dienes were carried out to afford highly functionalized cyclohexenes 4–9, bearing quaternary centers, in good yields. These cycloadducts (CAs) undergo dehydrochlorination with subsequent aromatization in the presence of 1,8-diazabicyclo[5.4.0]undec-7-e...

The title phosphorodiamidates are obtained in mixtures of Z and E isomers by phosphorylation of the corresponding alcohols followed by aminolysis.

A one-pot synthesis of new substituted allylic phosphorodiamidates was performed through phosphorylation of the corresponding alcohols followed by aminolysis. The intermediate allylic phosphorodichoridates could only be isolated when the starting allylic alcohol contains a trifluoromethyl group at the gamma-position. These phosphorodiamidates were...

New allylic phosphates were synthesized through phosphorylation of the corresponding alcohols. These compounds were obtained as mixtures of two (Z and E) isomers in 55-85% yield. They were characterized by multinuclear (1H, 13C, 31P, and 19F) NMR, IR spectroscopy, and HRMS.

New acylhydrazone derivatives 1–6 have been synthesized by condensation of tert-butylphenoxyhydrazide and cinnamaldehyde A or β-chloro-α,β-unsaturated aldehydes B–F. They were characterized by IR, (1H, 13C, 19F) nuclear magnetic resonance (NMR), and high-resolution mass spectroscopy. The NMR data show the existence of the cis/trans-amide conformers...

The Diels–Alder cycloaddition reactions of four β-chloro-α,β-unsaturated aldehydes 1–4 with cyclopentadiene were carried out. Only two of these aldehydes (3 and 4) were reactive and afforded highly functionalized norbornene isomers 5–10 in good yields. The Z-ethyl-2-chloro-3-formylacrylate 3 gave two diastereomers endo(COOEt)–exo(CHO) 5 and exo(COO...

The synthesis of octahedral complexes [SnCl4L2] (L = R2NP(O)(OCH2CF3)(O-p-tolyl): R2N = Me2N (1), Et2N (2), CH2(CH2CH2)2N (3), and O(CH2CH2)2N (4), or L = R2NP(O)(OCH2CF3)(O-p-PhNO2): R2N = Me2N (5), Et2N (6), and O(CH2CH2)2N (7) is described. The new adducts have been characterized by multinuclear (31P, 19F, 119Sn) NMR, IR spectroscopy, and elemen...

The reaction of SnCl4 with β-chlorovinyl aldehydes in anhydrous dichloromethane gave a series of octahedral complexes of the general formula SnCl4·2L (L = aldehyde). The adducts have been characterized in solution using multinuclear (1H, 13C, and 119Sn) NMR and IR spectroscopy. Solution NMR studies show that the complexes undergo rapid ligand disso...

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UDC 547-32;544.122;544.176;539.19 The synthesis of alkyl 2-chloro-3-formylacrylates 1 from alkyl pyruvates was carried out using Vilsmeier reaction. The reaction is highly stereoselective and leads to a 95:5 mixture of Z and E stereoisomers. Both stereoisomers were characterized by 1 H and 13 C NMR. In CDCl 3 solution, the NMR data, particularly th...

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The selective reduction of the trifluoro analog of the Hagemann’s ester 1 provided corresponding cyclohexenols, which underwent a Johnson–Claisen rearrangement leading to diesters 3. These latter are precursors of tetrahydroisochromanes 5 and octahydroisoquinoline 7a bearing an angular trifluoromethyl substituent.

The reactivity of the enolate of the 4-carbethoxy-3-trifluoromethyl-cyclohex-2-enone (1) toward electrophiles has been studied and compared with that of the parent Hagemann’s ester. Presence of the CF3 group could allow the selective introduction of substituents at three different sites. With alkyl halides the C-2 alkylation is completely favored....