bluuebunny/crossref_metadata_2025_split huggingface dataset:
A convenient synthesis of substituted piperazines via aminomercuration‐demercuration of diallylamines
Authors: Barluenga J. , Nájera C. , Yus M. 
Published: March 2009

Abstractcis and trans‐2,6‐Bis[bromomercuriomethyl]piperazines II which bear equal or different substituents at each nitrogen are obtained in the reaction of N‐substituted diallylamines with mercury(II) acetate and aryl‐amines followed by a double decomposition process with potassium bromide. Their reduction with sodium borohydride lead to the corresponding 1,4‐disubstituted cis‐ and trans‐2,6‐dimethylpiperazines III. Steric factors account for the remarkable stereoselectivity observed in the preparation of compounds IIIi‐IIIn in which a 3:1 cis to trans isomer ratio is found.
Analogs of propranolol. Synthesis of 3‐alkylamino‐1‐(3‐benzo[b]thienyloxy)‐2‐propanols
Authors: Conde Santiago , Corral Carlos , Lissavetzky Jaime 
Published: March 2009

AbstractThe synthesis by two alternative routes of 1‐(3‐benzo[b]thienyloxy)‐3‐isopropylamino‐2‐propanol hydrochloride (1a HCl), a thiophenic isoster of Propranolol, and related compounds, is reported. The protecting and enolizing properties of the 2‐methoxycarbonyl group on benzo[b]thiophene‐3‐one, along with its facile removal, are utilized in the first route. In the second one, conversion of 3‐bromobenzo[b]thiophene in 1‐(3‐benzo[b]thienyloxy)‐2,3‐o‐isopropylidenepropane is the key step. On the other hand, hydrolysis of 1‐(3‐benzo[b]furanyloxy)‐2,3‐o‐isopropylidenepropane to the corresponding diol, in order to obtain a furanic isoster of Propranolol (17a), was unsuccessful.
Synthesis and spectral data of some heterocyclic compounds. The reaction of arylpropiolic esters with tetralones and acetylcyclopropane
Authors: Al‐Jobour Nazar H. , Shandala Mowafaq Y. 
Published: March 2009

AbstractReaction of phenylpropiolic ester (I) with α‐ and β‐tetralones in the presence of sodium ethoxide yielded 5,6‐dihydro‐7,8‐benzflavones and ethyl β‐(2‐tetralon‐1‐yl)cinnamates, as a result of Claisen and Michael reactions, respectively. The reaction of I with 3‐ethoxy‐2‐cyclohexen‐l‐one and acetylcyclopropane in the presence of sodium ethoxide yielded acetylenic β‐diketones and 2‐aryl‐6‐cyclopropylpyran‐4‐ones, respectively. These products were identified on the basis of spectral and analytical data.
Synthesis of phenylurethans of a pyrazolidinylcarbinol as anticonvulsant agents
Authors: Kornet Milton J. 
Published: March 2009

AbstractEleven phenylurethans were prepared from 1,2‐dimethyl‐3‐hydroxymethylpyrazolidine and various phenyl isocyanates. Anticonvulsant screening revealed that two of the phenylurethans exhibited moderate activity in the maximal electroshock seizure (MES) test in mice.
Derivatives of 2‐sulfonamido‐4,5‐dimethoxyphenylacetic acid and of 2‐carboxamido(2‐chloroethyl)methylbenzenesulfonamides
Authors: Catsoulacos P. , Camoutsis Ch. 
Published: March 2009

AbstractSeries of variously sustituted amides of 2‐sulfonamido‐4,5‐dimethoxyphenylacetic acid have been prepared. The reaction of diethylamine, piperidine, morpholine and bis(2‐chloroethyl)amine with carbo‐methoxymethyl‐3,4‐dimethoxybenzenesulfonyl chloride produced the corresponding sulfonamido derivatives. Acid hydrolysis of the latter and action of thionyl chloride gave the chlorocarboxymethyl‐benzenesulfonamides. The acid chlorides of the sulfonamides were transformed to the 2‐carboxamido‐bis(2‐chloroethyl)methylbenzenesulfonamides with bis(2‐chloroethyl)amine. These agents were tested in L‐1210 and P‐388 leukemias and were found not to possess antitumor activity in these two transplantable tumor lines.
β‐Dicéto énamines hétérocycliques: 2. (Pyridyl‐4)‐2 indanediones‐1,3 C‐et N‐substituées
Authors: Ploquin J. , Sparfel L. , Le Baut G. , Floc'h Et R. 
Published: March 2009

AbstractLa substitution des (pyridyl‐4)‐2 indanediones‐1,3 conduit généralement à des composés N‐substitués. Ceux‐ci peuvent être obtenus également par condensation des pyridines mono‐ ou pluriméthylées sur les phtalates symétriques, mixtes ou acides et par condensation oxydative de bromures de N‐alkyl pyridinium sur l'indanedione‐1,3. La solvatochromie négative, observée dans les spectres electroniques de ces derives N‐substitués, traduit la prédominance d'une forme limite bétainique dans ces composés.
Photolyse d'oxaziridines. 10. Photolyse et thermolyse d'oxaziridines N‐arylées
Authors: Oliveros Esther , Rivière Monique , Lattes Armand 
Published: March 2009

AbstractLa régiosélectivité de la formation de lactameg par photolyse ou thermolyse des spirooxaziridines est indépendante de la nature du substituant sur l'azote. La thermolyse des oxaziridines N‐arylées constitue une méthode de synthèse de choix d'hétérocycles N‐aromatiques.
Steroidal thiadiazines
Authors: Kallias Dimitrios , Stassinopoulou C. I. , Catsoulacos Panayotis 
Published: March 2009

AbstractThe reaction of 16α‐bromoketosteroids, 2α‐bromoketosteroids and 21‐bromoketosteroids with thiosemi‐carbazide in 2‐propanol produces the corresponding 2′‐amino‐1′,3′,4′‐thidiazinosteroids. Acetylation of the 2′‐aminothiadiazino‐compounds led to the diacetamidothiadiazinosteroids. The title compounds prepared were substantiated by examination of infrared and nuclear magnetic resonance spectra.
Synthesis of 4H‐3,1‐benzoxazin‐4‐ones and 4‐(3H)quinazolinones from anthranilic acids and their derivatives by the use of triphenyl phosphite and pyridine
Authors: Rabilloud Guy , Sillion Bernard 
Published: March 2009

AbstractA series of 2‐substituted 4H‐3,1‐benzoxazinones and 2,3‐disubstituted 4‐(3H)quinazolinones have been synthesized in mild conditions by the use of triphenyl phosphite and pyridine as cyclising medium. Benzox‐azinones are produced either by ring closure of 2‐(acylamino)benzoic acids or in the reaction of benzoic acid with anthranilic acids. In the presence of aniline, the reaction leads to quinazolinones.
The synthesis of 4‐substituted‐4H‐1,2,4‐triazole‐3‐thiols and 3‐methylthio‐4‐substituted‐4H,2,4‐triazoles
Authors: Lin Yang‐i , Petty S. R. , Lovell F. M. , Perkinson N. A. , Lang S. A. 
Published: March 2009

AbstractThe synthesis of 4‐substituted‐4H‐1,2,4‐triazole‐3‐thiols and 3‐methylthio‐4‐substituted‐4H‐1,2,4‐triazoles by the condensation of 4‐substituted‐3‐thiosemicarbazides with dimethylformamide dimethyl acetal or dimethylacetamide dimethyl acetal is described. A discussion of the mechanistic pathway is included.
Reaction of arylamidoximes with dimethyl acetylenedicarboxylate and diethyl chlorofumarate. Stereochemistry of the adducts and the derived 1,2,4‐oxadiazines
Authors: Guzmán Angel , Romero Susana , Urquiza E. M. Guadalupe , Muchowski Joseph M. 
Published: March 2009

AbstractIt was shown that the addition of benzamidoxime to dimethyl acetylenedicarboxylate was predominantly cis‐oid in methanol or acetonitrile solution and mainly trans‐oid when benzene was the solvent. The stereochemistry of the cis‐oid (4a) and trans‐oid (5) adducts was deduced by transformation into the oxadia‐zinones (7a and 8a) which, upon hydrolysis and subsequent reaction with acetic anhydride, gave the furo‐[2,3‐c]‐1,2,4‐oxadiazine (9) and the symmetrical anhydride (10), respectively.The reaction of diethyl chlorofumarate with the sodium salt of benzamidoxime produced the oxadiazinone (8c).
Internal oxidation‐reduction of quinoxaline‐2‐ carboxaldehyde 1,4‐dioxide
Authors: Kluge Arthur F. , Maddox Michael L. 
Published: March 2009

AbstractReaction of carboxaldehyde 1 with acetone cyanohydrin gives carboxylic acid 2. Reaction of 1 with acetone cyanohydrin in methanol affords the methyl ester 3. The structural assignment for 2 is supported by 13C nmr data and by the decarboxylation of deuterated 2 to give 4b. The internal oxidation‐reduction upon going from 1 to 2 is explained in terms of a mechanism whereby 1 is converted into its cyanohydrin 5 and then to acyl cyanide 6. Acyl cyanide 6 then reacts with either water or methanol to give 2 or 3.
Sur une attaque inhabituelle de l'hetérocycle du benzofuranne, par action de chlorure de sulfuryle sur l'acétamido‐3 nitro‐2 benzofuranne
Authors: Royer RenÉ , Risse Simone , Demerseman Pierre 
Published: March 2009

AbstractAu lieu d'effectuer la chloration escomptée, le chlorure de sulfuryle transforme l'acétainido‐3 nitro‐2 benzofuranne en acétylimino‐3 chloro‐2 nitro‐2 coumaranne. Lorsque la réaction est effectuée en présence d'un alcool, elle fournit en outre un acétamido‐3 alkoxy‐3 chloro‐2 nitro‐2 coumaranne.
Convenient total synthesis of (dl)‐quebrachamine
Authors: Giri Venkatachalam S. , Ali Esahak , Pakrashi Satyesh C. 
Published: March 2009

AbstractRacemic quebrachamine (1) has been synthesised from 2‐hydroxytryptamine and dimethyl 4‐ethyl‐4‐formylpimelate through 1,2‐dehydroaspidospermidine (8), obtained by selective reduction of the carbonyl function of lactam 3.
The reaction of β‐amino conjugated enones with trimethylchlorosilane
Authors: Kashima Choji , Yamamoto Yasuhiro 
Published: March 2009

AbstractBy the reaction of β‐amino conjugated enones with trimethylchloroailane, both amino acetophenone and pyridine derivatives were formed in good yield. The selectivity of the formation of the products depended on the bulkiness of the N‐substituents of β‐amino conjugated enones.
Sur la synthèse de quelques furochromènes, analogues pharmacochimiques de la xanthylétine et de la séseline
Authors: René Loïc , Faulques Michelle , Royer RenÉ 
Published: March 2009

AbstractSome furochromenes substituted at the 2‐position by an electron‐attracting group were obtained starting from ortho‐hydroxyformyl derivatives of 2,2‐dimethyl‐2H‐chromene following various processes which are indicated. These new furochromenes are pharmacochemical analogues of some natural pyranocoumarins, and as such they are potential photosensitizers.
Novel heterocycles. 5. Lactone fused quinazolines
Authors: Coppola Gary M. , Shapiro Michael J. 
Published: March 2009

AbstractQuinazoline fused lactones were synthesized. The six‐membered lactone 7 was prepared by the interaction of ethyl pyruvate with hydroxyethylanthranilamide 11, followed by hydrolysis and cyclization using 1‐methyl‐2‐choropyridinium iodide. The corresponding seven‐membered lactone 10 was prepared by reaction of 11 with ethyl propiolate, followed by hydrolysis and cyclization as above. Quinazolines possessing functionalities capable of forming either a six‐ or seven‐membered lactone were cyclized in xylene in the presence of sodium methoxide. Only the six‐membered lactone 14 formed.
Hydrazines et hydrazones heterocycliques. III. Synthese de derives du naphto[2,3‐d]thiazole
Authors: Leymarie‐Beljean Martine , Pays Michel , Richer Jean‐Claude 
Published: March 2009

AbstractOn rapporte la sythèse de l'hydrazino‐2 naphto[2,3‐d]thiazole, de l'hydrazone de la méthyl‐3 naptho[2,3‐d]‐thiazoline‐2 et de quelques (alkylidènehydrazino)‐2 méthyl‐3 naphto[2,3‐d]thiazoles correspondants. Les composés sont caractérisés par leurs spectres infrarouges, ultraviolets, rmn en présence d'Eu(fod)3 et de masse.
Reissert compound studies. XXXVI. Observations on 1,7‐, 4,6‐, 4,7‐, and 1,10‐phenanthrolines
Authors: Bhattacharjee D. , Popp F. D. 
Published: March 2009

AbstractReissert compounds have been prepared from 1,7‐, 4,6‐, and 4,7‐phenanthrolines. In the case of 4,7‐phenanthroline, both mono‐ and di‐Reissert compounds have been prepared. A number of Reissert analogs have also been prepared in this series. 1,10‐Phenanthroline fails to give a Reissert compound.
2‐Amino‐4‐aryl‐6‐(ω‐carboxyalkyl)‐5H‐pyrrolo[3,4‐d]pyrimidin‐7‐(6H)ones. Preparationviaa one‐pot synthesis of 1‐(ω‐carboxyalkyl)‐4‐carbethoxy‐2,3‐dioxopyrrolidines
Authors: Madhav R. , Snyder Carroll A. , Southwick Philip L. 
Published: March 2009

Abstract1‐(ω‐Carboxyalkyl)‐4‐carboethoxy‐2,3‐dioxopyrrolidines were prepared by a one‐pot synthesis from β‐alanine or γ‐aminobutyric acid, ethyl acrylate and diethyl oxalate. In a second one‐pot process these products were hydrolyzed, decarboxylated and condensed with aromatic aldehydes under the influence of hydrochloric acid to yield 1‐(ω‐carboxyalkyl)‐4‐arylidene‐2,3‐dioxo‐pyrolidines, which yielded 2‐amino‐4‐aryl‐6‐(ω‐carboxyalkyl)‐5H‐pyrrolo[3,4‐d]pyrimidin‐7‐(6H)‐ones upon treatment with guanidine. It was shown that 3,4‐dihydro derivatives of certain 2‐amino‐4‐aryl‐5H‐pyrrolo[3,4‐d]pyrimidin‐7‐(6H)ones, formed initially in the guanidine reaction, readily undergo conversion to 5H‐pyrrolo[3,4‐d]pyrimidin‐7‐(6H)ones.
The thermolysis of heterocyclic aminimines
Authors: Posvic Harvey , De Meireles Jorge C. 
Published: March 2009

AbstractAminimines derived from six heterocyclic tertiary amines were thermolyzed in t‐butyl alcohol at ca. 80°. N‐Methylindoline gave a good yield of the ring‐opened product, and a double elimination on 1,4,4‐trimethyl‐piperidine gave 3,3‐dimethyl‐1,4‐pentadiene. The aminimine derived from quinuclidine was stable to elimination under these conditions. Simple elimination products were not obtained from N‐methyl‐pyrrolidine, N‐methylpiperidine, or N‐methyltetrahydroisoquinoline.
Selenium‐sulfur analogs 2. Synthesis and characterization of 4‐aralkyl‐1,2,3‐selenadiazoles and ‐1,2,3‐thiadiazoles
Authors: Hanson Robert N. , Davis Michael A. 
Published: March 2009

Abstract1 The3‐diketones 5 and 8 were alkylated with methyl iodide to give the nonenolizable diketones 6 and 9 which condensed with semicarbazide hydrochloride yielding the monosemicarbazones 7 and 10. Cyclization with selenous acid or with thionyl chloride led to the corresponding 1,2,3‐selenadiazoles 3a, 4a, and 1,2,3‐thiadiazoles 3b, 4b.
Synthesis of phenanthro[b]thiophenes
Authors: Iwao Masatomo , Lee Milton L. , Castle Raymond N. 
Published: March 2009

AbstractAll isomers of the parent phenanthro[b]thiophenes, namely, phenanthro[1,2‐b]thiophene, phenanthro‐[2,1‐b]thiophene, phenanthro[2,3‐b]thiophene, phenanthro[3,4‐b]thiophene, phenanthro[3,4‐b]thiophene, phenanthro[4,3‐b]thiophene and phenanthro[9,10‐b]thiophene have been synthesized.
Diazapolycyclic compounds. XX. Stereochemistry of some addition reactions to the double bond at the terminal tetrahydropyridazine ring of methyl substituted 4a,12a‐diaza‐1,4,4a,5,12,12a‐ and 4a,12a‐diaza‐3,4,4a,5,12,12a‐hexahydronaphthacene‐5,12‐diones, and the corresponding epoxides
Authors: Cano M. C. , Contreras F. Gómez , Sanz A. M. 
Published: March 2009

AbstractThe stereochemistry of N‐bromosuccinimide electrophilic additions to the double bond at the terminal tetrahydropyridazine ring moiety of the 4a,12a‐diazatetracyclic compounds 1‐4 has been studied. These reactions appear as very regio‐ and stereoselective. Most the of the results obtained support the hypothesis that the N‐bromoamide additions to cyclohexenes and heterocyclic analogous do not occur via the usual AdE2 mechanism, because the nucleophilic step is the rate‐limiting one and the main product‐determining factor. On the other hand, epoxidation of the double bond in 1‐4 and further opening of the oxirane ring take place in accordance with the normal stereochemical rules.
3‐Oxo‐1,2‐benzoisothiazoline‐2‐acetic acid 1,1‐dioxide derivatives. I. Reaction of esters with alkoxides
Authors: Schapira Celia B. , Perillo Isabel A. , Lamdan Samuel 
Published: March 2009

AbstractReaction of 3‐oxo‐1,2‐benzoisothiazoline‐2‐acetic acid alkyl esters 1,1‐dioxide (1a‐d) with alkaline alkoxides was carried out under various conditions. Under mild conditions, o‐(N‐carboxymethylsulfamyl)benzoic acids dialkyl esters (2a‐d) were obtained with good yields. Reaction of 1a‐d or 2a‐d with sodium alkoxides under drastic conditions afforded 4‐hydroxy‐2H‐1,2‐benzothiazine‐3‐carboxylic acid alkyl esters 1,1‐dioxide (3a‐d). Transesterification was observed when esters 1b‐d were treated with sodium methoxide in methanol. Esters 3a‐d were hydrolyzed in concentrated aqueous sodium hydroxide affording the acid 6. Attempts to recrystallize 6 from water resulted in its decarboxylation to give 2H‐1,2‐benzothiazine‐4‐(3H)one 1,1‐dioxide (7). Compound 6 could not be obtained by acid hydrolysis of esters 3a‐d or by rearrangement of 3‐oxo‐1,2‐benzoisothiazoline‐2‐acetic acid 1,1‐dioxide (8). Different experimental evidence supports the suggestion that rearrangement took place by ethanolysis of the carboxamide linkage affording the open sulfonamides (fast step) followed by a Dieckmann cyclization (slow step). It was demonstrated that transesterification took place in the open sulfonamides 2.
Versatile and efficient synthesis of aryl‐1,2,3,4‐tetrahydroisoquinolines: Nickel(II) phosphine ligand catalyzed coupling of arylmagnesium halides to haloisoquinolines
Authors: Pridgen Lendon N. 
Published: March 2009

AbstractDichloro[1,3‐bis(diphenylphosphino)propane]nickel(II) (dppp) was used as catalyst to prepare some previously unreported arylisoquinolines 3, which were in turn hydrogenated to aryl‐1,2,3,4‐tetrahydroiso‐quinolines 2. This procedure is the most direct and efficient method currently available for the preparation of many compounds of the type 2 and 3.
Synthesis of 1,8‐ and 2,8‐dihydrocycloheptapyrazol‐8‐one derivatives by the reactions of 3‐acetyltropolone and its methyl ethers with phenylhydrazine
Authors: Imafuku Kimiaki , Yamane Akio , Matsumura Hisashi 
Published: March 2009

Abstract3‐Acetyltropolone (1) reacted with phenylhydrazine to give 3‐acetyltropolone phenylhydrazone (3) and 3‐methyl‐1‐phenyl‐1,8‐dihydrocycloheptapyrazol‐8‐one (4). The former (3) cyclized to afford the latter (4). The reaction of 3‐acetyl‐2‐methoxytropone (2a) with phenylhydrazine gave 4, 3‐methyl‐2‐phenyl‐2,8‐dihydrocyclo‐heptapyrazol‐8‐one (5), and 3‐methyl‐2‐phenyl‐2,8‐dihydrocycloheptapyrazol‐8‐one phenylhydrazone (6). The compound (5) reacted with phenylhydrazine to afford 6. The reaction of 7‐acetyl‐2‐methoxytropone (2b) with phenylhydrazone gave 7‐acetyl‐2‐methoxytropone phenylhydrazone (7), 7‐acetyl‐2‐(N′‐phenylhydrazino)‐tropone phenylhydrazone (8), 3‐methyl‐1‐phenyl‐1,8‐dihydrocycloheptapyrazol‐8‐one phenylhydrazone (9), and 6. The compound (7) was heated to afford 4 and reacted with phenylhydrazine to afford 8 and 9. The compound (8) was also refluxed to give 9.
Synthesis of 2‐substituted styryl‐6‐bromo‐4‐quinazolone 3‐(4‐benzhydrazides) as possible monoamine oxidase inhibitors
Authors: Misra R. S. , Dwivedi C. , Parmar S. S. 
Published: March 2009

AbstractNine ethyl 2‐substituted styryl‐6‐bromo‐4‐oxoquinazoline‐3‐(4‐benzoates) were prepared by condensing bromoacetanthranil with ethyl‐4‐aminobenzoates. These esters were converted to the corresponding hydrazides with hydrazine hydrate in order to study their monoamine oxidase inhibitory and anticonvulsant properties.
The synthesis of 3H‐pyrazol‐3‐one derivatives containing a 9H‐xanthene ring
Authors: Okabayashi Ichizo 
Published: March 2009

Abstract2,4‐Dihydro‐5‐methyl‐2‐phenyl‐4‐(9H‐xanthen‐9‐yl)‐3H‐pyrazol‐3‐one (3) was prepared by the condensation of phenylhydrazine and ethyl α‐acetyl‐9H‐xanthene‐9‐acetate (2), or 9H‐xanthen‐9‐ol (1) and 2,4‐dihydro‐5‐methyl‐2‐phenyl‐3H‐pyrazol‐3‐one (4). 5‐Amino‐2,4‐dihydro‐2‐phenyl‐4‐(9H‐xanthen‐9‐yl)‐3H‐pyrazol‐3‐one (6) was obtained by the condensation of 1 and 5‐amino‐2,4‐dihydro‐2‐phenyl‐3H‐pyrazol‐3‐one (5).
Mannich's arsindole (1,3‐dichloro‐2‐diethylaminomethylbenzo[b]arsole hydrochloride). Ultraviolet spectrum and behaviour on electron impact. A comparison with other heterocyclic and acyclic chloroarsines
Authors: Allen David W. 
Published: March 2009

AbstractThe ultraviolet and mass spectra of the title compound have been recorded and compared with those of 2‐chloro‐2‐phenylvinyldichloroarsine (and other chloroarsines). The spectra of the arsindole resemble those of related indoles, phosphindoles and other aromatic heterocyclic systems, and are markedly different from those of the above acyclic chloroarsine, indicating the probable involvement of arsenic in a cyclic π‐delocalised system.
Synthesis and photopinacol rearrangement of 1a,9a‐dihydro‐1a,9b‐diphenylphenanthro[9,10‐b]oxirene
Authors: Avnir Davis , Blum Jochanan 
Published: March 2009

AbstractThe synthesis of the title compound is described. Pinacol reduction of 2,2′‐dibenzoylbiphenyl followed by dehydration of the trans‐diol, so formed, with dimethylformamide dimethyl acetal yielded 55% of the oxirane. Irradiation of the oxide in methylene chloride at 254 nm gave 10,10‐diphenyl‐9‐(10H)phenanthrone as the major photoproduct.
The first examples of the 11H‐[2]benzazepino[1,2‐a]dibenz[b,f]azocine ring system
Authors: Schwan Thomas J. 
Published: March 2009

AbstractThe ring closure of 2‐[(11,12‐dihydro‐6‐oxodibenz[b,f]azocin‐5‐yl)methyl]benzoic acid in polyphosphoric acid to 16,17‐dihydro‐11H‐[2]benzazepino[1,2‐a] dibenz[b,f]azocine‐4‐(9H)‐11‐dione is reported. Degradation studies supporting this structural assignment for the annelation product are described.
Thiophene systems. 4. Selective syntheses of thieno[3,4‐b][1,4]‐ and [1,5]benzodiazepinones
Authors: Press Jeffery B. , Hofmann Corris M. , Safir Sidney R. 
Published: March 2009

AbstractNovel syntheses of thiophene fused tricyclic systems 1 and 2 are reported. The methods use intermediates 4‐ethoxy‐3‐thiopheneamine, 4‐ethoxy‐3‐thiophenecarbonyl aside and 4‐ethoxy‐3‐thiophenecarbonyl chloride to effect selective, high yield syntheses of the target compounds in two steps. These methods allow preparation of thiophene systems without substitution at the normally reactive C‐1 and C‐3 positions.
Action des dihydro‐4,5 oxazoles‐1,3 sur le dioxy‐2,2 oxathiolane‐1,2 I. Synthèse et caractérisations du (méthyl‐2 oxazolinium‐1,3)‐3 propanesulfonate
Authors: Forestière A. , Sillion B. 
Published: March 2009

AbstractL'addition de la méthyl‐2 oxaxoline‐1,3 (1a) sur la propanesultone‐1 (3) (2) conduit à un composé ionique de type sulfobétaïne 4a que nous avons caractérisé par spectroscopie. La structure proposées est confirmée par quelques réactions chimiques de ce composé.
Syntheses with nitriles. 60. Preparation of 4‐amino‐5‐cyano‐6‐phenylpyrimidines from 2‐amino‐1,1‐dicyano‐2‐phenylethene
Authors: Mittelbach Martin , Junek Hans 
Published: March 2009

AbstractThe reaction of 2‐amino‐1,1‐dicyanobut‐1‐ene and 2‐amino‐1,1‐dicyano‐2‐phenylethene, respectively, with N,N‐dimethylformamide dimethylacetal provided the corresponding (N,N‐dimethylaminomethylene)amino derivatives. 2‐[(N,N‐Dimethylaminomethylene)amino]‐1,1‐dicyano‐2‐phenylethene was converted into 4‐amino‐5‐cyano‐6‐phenylpyrimidines by treatment with primary aliphatic and aromatic amines. The structure of the reaction products was confirmed by 13C nmr spectroscopy.
[1]Benzothienopyrimidines. II. Study of the electrophilic substitutions of [1]benzothieno[3,2‐d]pyrimidine and [1]benzothieno[3,2‐d]pyrimidin‐4‐(3H)one
Authors: Rault Sylvain , De Sévricourt Michel Cugnon , Touzot Paulette , Robba Max , El‐Kashef Hussein 
Published: March 2009

AbstractThe nitration and bromination of both [1]benzothieno[3,2‐d]pyrimidin‐4(3H)one (1) and [1]benzothieno‐[3,2‐d]pyrimidine (2) has been studied. Nitration of 1 at −30° afforded a mixture of 8‐nitro[1]benzothieno‐[3,2‐d]pyrimidin‐4(3H)one (7b) (70%) and 6‐nitro[1]benzothieno[3,2‐d]pyrimidin‐4(3H)one (7a) (30%). However when the nitration was carried out at 60°, the 6,8‐dinitro derivative 8 was the result. On the contrary, the nitration of 2 at −30° gave a single nitration product, 8‐nitro[1]benzothieno[3,2‐d]pyrimidine (11). The bromination of both 1 and 2 gave the corresponding 8‐bromo derivatives 10 and 13. Assignment of structure of all the products was based on ir and nmr spectral studies and on unequivocal syntheses.
Synthesis of 2,3‐dihydro‐1H‐imidazo[1,2‐b]pyrazoles
Authors: Pilgram Kurt 
Published: March 2009

AbstractTwo novel 2,3‐dihydro‐1H‐imidazo[1,2‐b]pyrazole derivatives 7 and 8 have been prepared by hydrazinolysis with 2,4‐dinitrophenylhydrazine of 1‐(benzylideneamino)‐2‐(2‐ethoxycarbonyl‐2‐nitromethylidene)‐imidazolidine 4. The precursor 4 was conveniently prepared from ethyl nitroacetate and 1‐(benzylidene‐amino)‐2‐(methylthio)imidazoline 3. Two examples are presented in which ethyl aceto(and trifluoroaceto)acetate 2‐nitrophenyl‐hyrazone, 9 and 10, both of which also feature the β‐hydrazinoacrylate arrangement, are refluxed in ethanol containing hydrochloric acid and thereby converted into pyrazolones 11 and 12, pyrazoles 13 and 14, and ketone 2‐nitrophenylhydrazones 15 and 16, respectively.