JOURNAL of the Tunisian Chemical Society

serving the Research, the Education and the Industry

Condensation of iminoethers with diarylnitrilimines. Novel synthesis of 1,2,4-triazoles

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Condensation of iminoethers 3a-c with diarylnitrilimines 2a-d led to the corresponding 1,2,4-triazoles 5a-i in good yields. A probable mechanism was proposed for the reaction and the structure of all obtained products was determined on the basis of their analytical data: 1H, 13C NMR and mass spectrometry.

A. Romdhane, R. Gharbi, Z. Mighri

Iminoethers, Diarylnitrilimines, 1,2,4-Triazoles

Pages 189-192

Condensation du cyclopentadiénure de sodium sur des dérivés halogénoaromatiques

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The reaction of sodium cyclopentadienide was studied with three mono-halogenated models: 4-chloro-diphenylsulforie, 4-fluorobenzophenone and 4-chloro-trifluorotoluene. In spite of the absence of mobile hydrogen atoms in their structures, the reaction of these substrates with cyclopentadienide carbanion leads to a mixture of dienes di or trisubstituted and some of their dimmers obtained by Diels-Alder reaction which are identified by Gas Chromatographic/ MS coupling (GC-MS) and Liquid Secondary Ton Mass Spectrometry (LSIMS). A mechanistic interpretation was proposed for each case.

O. Mzani, H. Ben Romdhane, M. Baklouti

biscyclopentadienes, cyclopentadienide, nucleophilic aromatic substitution.

Pages 199-211

Cycloaddition dipolaire-1,3 du 2-diazopropane sur des maléimides N-substitués. Photochimie des adduits résultants

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The 1,3-dipolar cycloaddition of 2-diazopropane 1 with the N-substitued maleimides 2a-b at 0°C. has led to monoadducts Δ2-pyrazolines 3a-b. On the other hand the same reaction is carried out under similar operating conditions with maleimide 2c, has led to a new and unexpected heterocyclic structure 4c next to Δ2-pyrazolines. The photolysis of 3a-c has led to a cyclopropylketones 5a-c.

N. Ben Hamadi, J. Lachheb, A. Khemiss

2-diazopropane, Δ2-pyrazoline, photochemistry, cyclopropylketone

Pages 213-218

Structures de deux triterpènes, d'un stéroide et d’un hétéroside isolés de la plante Cardopatium amethystinum poussant en Tunisie

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Lupeol 1, lupeol palmitate 2, stigmasterol 3 and sitosterol 3β–O–[β–D-glucoside] 4 have been isolated and identified for the first time in the Cardopatium amethystinum plant. Their structures have been established by spectroscopic means.

H. Boukamcha, H. Ben Jannet, Z. Mighri

Cardopatium ametitystinum, Compositae, triterpenoids, heteroside, 2D NMR

Pages 219-227

Synthèse de dérivés 11-hydroxylés de la 6-oxo-6H-[1]-benzopyrano[4,3-b]quinoléine

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The reaction of 4-(2-hydroxyarylamino)coumarines 4 with N,N-dimethylformamide dirnethylacetal 5 provided 11-hydroxy-6-oxo-6H-[1]-benzopyrano[4,3-b]quinoline derivatives 8 via intramolecular cyclisation of non-isolable enaminic intermediate 6. Ring closure of 6 into benzopyrano-benzoxazepinone 7, however, failed.

B. Trimeche, R. Gharbi, Z. Mighri, M. T. Martin

4-hydroxycoumarine, 2-aminophenol, N,N-dimethylformainide dimethy lacetal, 6-oxo-6H-[1]- benzopyrano[4,3-b]quinoline

Pages 229-235

Synthèse de 2-amino-3-phosphonothiophènes

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The reaction of aliphatic or cyclic ketones 1 with phosphonoacetonitriles 2 leads to phosphonoalkylidenes 3. The reaction of compounds 2 with sulfur in basic conditions leads to the new 2-amino-3-phosphonothiophenes 4. Two diastereomers are obtained in some cases.

N. Said, S. Touil, H. Zantour

phosphonoacetonitriles, phosphonoalkylidenes, 2-arnino-3-phosphonothiophenes

Pages 237-243

Etude de l’activation des réactions anioniques par la catalyse par transfert de phase

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Anionic activation via addition of a phase transfert catalyst promotes anionic bimolecular reactions, such as ketolisation, ketoaldolistion, Baylis-Hillman, Cannizzaro reactions and addition of carbenes to ethylenic bonds. Mechanisms are proposed.

Y. Moussaoui, R. Ben Salem

catalyse par transfert de phase, mécanisme réactionnel, cétoaldolisation, Baylis-Hillman, Cannizzaro

Pages 255-263

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