Hétérocyclisations intramoléculaires par réaction d'oxymercuration. IV. Obtention d'alcools par fonctionnalisation des organomercuriques

It has been possible to functionalize heterocyclic organomercuric compounds by an oxidation reduction reaction. Tetrahydrofurfuryl alcohols have been obtained.     

Hétérocyclisation intramoléculaire par réaction d'oxymercuration. II. Oxymercuration intramolécuxlaire des allyl-2 cyclohexanols cis et trans

The intramolecular oxymercuration of two isomeric 2-allyl-cyelohexanols, has been realized with different mercuric salts. The reaction is always regiospecific, but not stereoselective, and leads to five membered mercurated heterocyclic. The reduction of organomercury compounds obtained from trans-2-allylcyclo-hexanol leads, in some cases, to a ring rearrangement, that permit us to obtain from the trans cyclised product, under different conditions either pyran or furan compounds.     

Hétérocyclisations intramoléculaires par réaction d'oxymercuration III. Régiosélectivité et stéréosélectivité de l'oxymercuration intramoléculaire de phénols orthoallyliques

The intramolecular heterocylization of ortho-allylic phenols by oxymercuration has been realized with compounds having different substituents on the allylic chain. In all cases, only the corresponding benzofuran is formed. However, with a substituent at the terminal carbon of the double bond, we also observed the formation of benzopyran. The influence of the solvent and the mercuric salt on the orientation of this reaction has been examined. There is evidence of a molecular rearrangement during the reduction.     

Synthèse d'hétérocycles en catalyse par transfert de phase

A general study of the chemical behavior of heterocyclic anions, dianions and dianionic reagents under phase transfer catalysis conditions allowed us to synthesize various heterocyclic compounds such as imidazo[2,1-b]thiazole and derivatives; imidazo[2,1-b]thiazine and imidazo[2,1-b]benzothiazepine. Reaction conditions e.g., catalyst, solvent, temperature, etc., are indicated.     

Synthèse, à partir du (+) — camphre,d'hétérocycles dérives des tétrahydroxanthone,tétrahydroacridone,tétrahydroacridine et octahydroacridine

Derivatives of acridine, acridone and xanthone were prepared from (+)-camphor, 3-Arylidene, 3-arylmehtyl or 3-aroylcamphors with an halogen in the ortho position and dibornanonylarylmethanes may be uased aas precursors. Ring closure may be induced by ammonia, armoatic amines or potassium hydroxide with or without a catalyst. Good yaields were obtained. In come casaes, the reaction goes with an aromatisation of the heterocyclic moiety.     

Un nouvel hétérocycle telluré: le benzisotellurazole-1,2. I. Synthèse et propriétés

Two different synthetic methods for 1,2-benzisotellurazole are described. The properties of this new heterocyclic system are compared with the analogous sulfur and selenium heterocycles.     

Synthèse photochimique de biaryles et hétérobiaryles à partir d'aryl-et hétéroarylamines,d'un nitrite d'alkyle et d'un substrat aromatique ou hétéroaromatique

Photochemical synthesis of biaryls and heterobiaryls from aryl and heteroarylamines, alkylnitrite and aromatic or heteromatic substrates The photochemical reaction of aromatic and heteroaromatic amines with excess t-butyl nitrite in aromatic solvents (benzene, p-xylene, mesitylene) and in hetero-aromatic solvents (furan, thiophene) leads to biaryls or heterobiaryls. t-Butyl nitrite is more convenient than isopentyl nitrite which gives by-products. This new method has been used to synthesize 28 compounds in 17 to 60% yield.     

Addition d'hétérocycles azotés aux alcynes arylés; synthèse de N-styrylazoles

Azoles (pyrazoles imidazoles) add to the triple bond of phenyl-acetylene and phenylmethylacetylene according to stereoselective and sterospecific addition. In this manner various styrylazoles have been synthesized.     

Hétérocycles contenant du phosphore. XXIII—Etude par RMP de dérivés de l'oxazaphospholane-1,3,2: III—Interprétation des résultats. Tentative d'analyse conformationnelle

By employing certain hypotheses, it is possible to determine the C₄? C₅ conformation of the various 1,3,2-oxazaphospholane derivatives for which PMR parameters have been calculated previously.     

Une synthèse générale des tétraazamacrocycles mono-C-fonctionnalisés

A General Synthesis for Mono-C-Functionalized Tetrazamacrocycles A new synthesis, under usual conditions of concentration, medium, and temperature, of a series of mono-C-functionalized tetraazamacrocycles is given. The method may easily be generalized. The new procedure allows the modification of the length of the side-chain or the size of the cavity by choosing fitted staring materials. The key intermediate has a tosylated linear side-chain susceptible to be transformed into a large variety of functional groups.     

Hétérocycles des Eléments du Groupe IV. VII—Spectrométrie de Masse de Silacyclopentènes

Mass spectra of substituted silacyclopentenes have been studied. The fragmentation mechanisms observed are similar to those for germacyclopentenes. The most important conclusions are retention of the charge on the heteroatom, hydrogen migration, silyl ion formation and expulsion of substituents linked on the heteroatom.     

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.     

Stéroidohétérocycles: Hétérocycles azotés a 5,6 et 7 chainons accolés simultanément aux cycles A et B d'un stéroide par les positions 4,5 et 6

New systems with five, six or seven membered nitrogen hetero-cycles (pyrazole, pyrimidine or diazepine) simultaneously fused to the 4, 5 and 6 positions of the two A and B rings of a cholestane derivative have been prepared.     

Nucléosides de synthèse XIV. Du choix des paramètres réactionnels pour l'obtention préférentielle de nucleosides en série benzoazole par réaction de fusion

By a judicious choice of the fusion reaction parameters, mainly the percentage of catalyst, we have obtained the corresponding benzotriazole and benzimidazole nucleosides substituted at N-2. We have also obtained the α N-1 anomers. Thus, we have shown it is possible, to confer some selectivity to the acid-catalyzed fusion-reaction.     

Synthèse de composés comportant deux hétérocycles oxygénés accoles au noyau benzénique, éthers du résorcinol

We wish to report the preparation of new bisheterocyclic compounds derived from resoreinol. We tried to sue methods during this investigation which would be selective and afford only tricyclic linear compounds. The starting material was resorcinol or the monomethylether of resorcinol. By reaction with chloroacetonitrile, acrylonitrile or ethyl chlorobutanoate, we obtained the intermediate compounds which were then cyclized by reaction with sodium acetate or polyphosphoric acid; either a catalytic reduction or treatment with zinc in presence of hydrochloric acid furnished the heterocyclic base. Another condensation followed by a cyclization and a reduction gave the desired compounds.     

Nouvelle synthèse des composés polysubstitués d'esters de l'acide pyrrolecarboxylique-3 par réarrangement d'époxy-1,2 pyrrolidines

In presence of acides (HF/pyridine) substitutes 3-ethoxycarbonyl-6-oxal-azabicyclo[3.1.0[hexanes 1 afforded subtituted 3-ethoxycarbonyl-pyrroles 3 in stereospecific manner. Spiro substrates gave polycyclic product under the conditions used.     

Condensation du méthane disulfochlorure avec quelques diamines 1,2 et 1, 3 études des hétérocycles obtenus

Bis ehlorosulfonylmethane was condensed with several ortho-phenylendiamines in benzene at low concentration, yielding the corresponding bcnzo[e]-1,3,4,7-dithiadiazepine 2,2,4,4-lrtroxides. A similar heterocycle was obtained from bischlosulfonylmethane and 2-amino-5-chlorobenzhydrylamine. Mass spectrometry results were discussed with reference to one of the series.     

Synthèse d'hétérocycles dérivés du (+)-camphre

Diamines react with 3-dimercaptomethylenecamphor giving either a bis-oxothioamide or a heterocyclic compound via in oxoaminothioamide intermediate. In this last reaction, there is cleavage of both C? S bonds. Similarly, diamines react with β-oxothioamides to produce the same heterocyclic derivatives. In these reactions, a transamination is involved and the carbonyl group of camphor is preserved. A distinctly different reaction occurs when the same camphor derivatives are treated with hydrazine; thioxo- alcoylamino- or arylaminoindazoles are then obtained. Ring closure occurs on the carbonyl carbon of the camphor molecule.     

Synthèse d'amines hétérocycliques,cancérostatiques potentiels

We report the nitration of various heterocycles containing two heterocyclic nitrogen atoms. The amines obtained by reduction have been characterized and the fact that the amines have been tested for anticancer activity is also reported.