Synthèse de céphalosporine-lactones

Condensation of azetidinones 2a and 2b with mercaptan 3 gave respectively compound 10 or a 1:1 mixture of 17 and 17 ′. Bromination of 10 , afforded cis and trans-bromohydrins 13a and of 17 and 17 ′ cis and trans-bromohydrins 18a . Acetylation and reduction with zinc and acetic acid of these bromohydrins gave cephems 4a or 4b and 4b ′ respectively.     

Synthèse et transformations de pyridopyrimidopyrimidines

A convenient one-step synthesis of a pyridoprimidopyrimidine system by means of the chloride of 1,3-dimethy1-4amino-5-amino-5-(N,N-dimethyliminiumchloromethine)uracil and substituted pyridines is studied and the title compounds are described.     

Synthèse de l'évernine

Synthesis of Evernin Two syntheses of the depside evernin 6 are described. Condensation of methyl acetoacetate and methyl crotonate followed by aromatization and reduction with Raney-Ni led to methyl orsellinate (3) . The condensation of everninic acid (4) , obtained by partial methylation of 3 and saponification of the methyl ester, with methyl 2, 4-dihydroxy-3, 6-dimethylbenzoate (methyl β-orcin carboxylate) (5) in presence of cyclohexylcarbodiimide gave evernin ( 6 ). In a second syntheis methyl dihydroorsellinate (1) was regiospecifically converted into its 4-methyl enol ether and aromatized via the benzene selenenyl derivative to yield methyl evernate (7) . Benzylation followed by saponification gave the free acid 8 . Methyl β-orcin carboxylate (5) was synthesized in an analogous way from methyl 3,6-dimethyl-2,4-dioxocyclohexanecarboxylate. Condensation of 8 with the methyl ester 5 by treatment with trifluoroacetic anhydride in toluene yielded 9 , which could be converted into evernin ( 6 ) by hydrogenolysis of the benzyl ether.     

Synthèse de l'ériodermine

Synthesis of Eriodermin The total synthesis of eriodermin (=2,7-dichloro-4-formyl 3-hydroxy-8-methoxy-1,6-dimethyl-11H-dibenzo[b,e] [1,4]dioxepin-11-one) is described.     

Synthèse de l'acide décarboxythamnolique

Synthesis of Decarboxythamnolic Acid The total synthesis of the meta-depside decarboxythamnolic ( = 3-[(3-formyl-2-4-dihydroxy-6-methyl-phenyl)oxy]-2-hydroxy-6-methoxy-4-methylbenzoic acid; 25 ) by the biomimetic condensation of the substituted β-orcinol units 9 and 22 is described.     

Synthèse d'iodopyrroles

This article reports the synthesis of di- and triiodopyrroles by reduction of tetraiodopyrrole. A new synthesis of 4-iodo-3- formylpyrrole is described.     

Synthèse d'analogues acycliques de C-nucléosides

A direct method for the preparation of 2-hydroxyethoxymethyl derivatives of guanine and s-triazolo[1,5-a]pyridine in which the chain is joined into the heterocyclic base by a carbon-carbon bond is describe.     

Synthèse du virensate de méthyle

Synthesis of Methyl Virensate The synthesis of methyl virensate (=methyl 4-formyl-3,8-dihydroxy-1,6,9-trimethyl-11-oxo-11H-dibenzo-[b, e][1,4]dioxepin-7-carboxylate; 18 ) by the condensation of the substituted β-orcinol and orcinol units 9 and 10 followed by formylation and demethylation of the depsidone 13 is described.     

Synthèse de l'amino-3 azétidine

The synthesis of a novel heterocyclic compound, 3-aminoazetidine as a potential pharmacophore belonging to piperazine or 4-aminopiperidine structural classes, is described. The method is based on a phase-transfer catalysed nucleophilic alkylation of potassium phthalimide.     

Synthèse et structure de benzopyranno-1 triazines-1,2,4

Under basic conditions 2,2,6-trimethyl-3,4-chromanedione is cy8clised nto I-benzopyranno[4,3-e]triazin-3-one. In acetic meduum, semicarbazide hydrochloride and diketone provide the I-benzopyranno[4,3-e] and [3,4-e]triazin-3-ones. However, under the same conditions, the thiosemi-carbazide leads exclusively to the I-benzopyranno[4,3-e]triazine-3-thione. The structure of these compounds is in agreement with the ¹³C nmr spectra.     

Synthèse de sucres aminès ramifiés II. Synthèse et réactions de spiro-aziridines. Communication préliminaire

Treatment of 3-C-cyano-1,2:5,6-di-O-isopropylidene-3-O-(toluene-p-sulfonyl)-α-D -allofurannose with AlLiH₄ or RMgX yields spiro-aziridines with two identical substituents on C(3′) (? H, ? CH₃, ? C₂H₅). Reactions of these products and their derivatives are briefly described. If the C(3′) substituents are protons, the aziridine ring is easily opened. In acidic media (HCl), an amino-sugar containing the branched chain ? CH₂Cl is produced; with hydrogenation, a ? CH₃ branched chain results. If the C(3′) substituents are methyl groups, the aziridine ring cannot be opened neither with HCl nor with hydrogen. The acetylated derivative of this latter compound rearranges to the corresponding allylamide with HCl. For both types of spiro-aziridine, the nitrous deamination leads to the corresponding alkene.     

Synthèse de la diméthyl-4,4-dihydrofuranedione-2,3

4,4-Dimethyl-dihydro-2,3-furanedione ( 4 ), an intermediate in the synthesis of (+)-D -pantothenic acid, is obtained in good yield from readily available substances such as isopropyl chloride, diethyl oxalate and formaldehyde, without oxidative conditions.     

Synthèse et réactivité de dihydrotriazines et de dihydrotriazolotriazines

Generally, 4,5-dihydro-3triazinones have been prepared by a basic hydrolysis of 3-methylmercapto-4,5-dihydrotriazines. Of the serveral methylation methods, namely, diazomethane, methyliodide, dimethyl sulfate all in the presence of sodium methylate or silver carbonate, only methyl bromide in the presence of phase transfer catalyst was sucessful in producing all of the N-2 and/or N-4 methylate compounds. Two unequivocal syntheses of dihydrotriazolo[4,3-b]triazine are reported.     

Synthèse de nouveaux hétérocyeles indoliques

In this work we present a new aproch for the synthesis of tri aned tetracyclic heterocycles in the indole series.     

Synthèse et réactivité de nitro indazoles

Synthese and nmr study of forty-four nitroindazoles in which twentry-three were never published have been carried out. The best way to obtain the halogenomethyl derivatives(halogenation before or after methylation) is shown. Relative reactivities of the different heterocyclic ring positions toward the electrophilic agent are discussed.