bluuebunny/crossref_metadata_2025_split huggingface dataset:
1,3‐Dipolar cycloaddition synthesis of 3‐bromo‐5‐substituted isoxazoles, useful intermediates for the preparation of pharmacologically active compounds
Authors: Chiarino D. , Napoletano M. , Sala A. 
Published: April 2009

AbstractBromonitrile oxide 2, generated from easily available dibromoformaldoxime 1, reacts with monosubstituted acetylenic derivatives 4 to give 3‐bromo‐5‐substituted isoxazoles 5 in high yield. The experimental conditions necessary to overcome difficulties such as the low reactivity of acetylenic dipolarophiles and the high tendency to dimerization of bromonitrile oxide 2, are discussed; the regioselectivity of this 1,3‐dipolar cycloaddition is also studied. The obtained improvements in the synthesis of some pharmacologically active compounds are reported.
Some chemical transformations of 7a‐cyanohexahydro‐1H‐pyrrolizine into 7a‐substituted hexahydro‐1H‐pyrrolizines
Authors: Miyano Seiji , Yamashita Osamu , Sumoto Kunihiro , Shima Keiyu , Hayashimatsu Mariko , Satoh Fumio 
Published: April 2009

AbstractChemical transformations of 7a‐cyanohexahydro‐1H‐pyrrolizine (2) into 7a‐substituted hexahydro‐1H‐pyrrolizines are described. In the reaction of 2 with lithium aluminum hydride, the orientation of the lone pair of the bridgehead nitrogen against C‐CN bond can be regarded as significant.
Nitration of some 3,5‐disubstituted pyridine N‐oxides
Authors: Bissell Eugene R. , Swansiger Rosalind W. 
Published: April 2009

AbstractThe preparation of 3‐chloro‐5‐methoxypyridine N‐oxide and its nitration are reported. Mononitration yields 5‐chloro‐3‐methoxy‐2‐nitro‐pyridine N‐oxide while more drastic conditions give 3‐chloro‐5‐methoxy‐2,6‐dinitropyridine. Removal of various substituents by base hydrolysis is also discussed.
Meerwein arylation of methyleneglutaronitrile with anthraquinone diazonium hydrogensulfate. Synthesis of an enolizable benzanthrone lactone
Authors: Sutter P. , Weis C. D. 
Published: April 2009

AbstractThe Meerwein reaction of 1‐anthraquinone diazonium hydrogensulfate with 2‐methyleneglutaronitrile in methanol yielded predominantly 3‐hydroxy‐4‐(1‐anthraquinone)‐1,3‐butanedicarbonitrile (5), while the corresponding 2‐methyleneglutaric acid diethyl ester furnished a derivative of 1‐(anthraquinone)butanolide 10. Catalytic dehydrocyanation of 5 was effected with Dowex‐50 to furnish 3‐oxo‐4‐(anthraquinone)butanecarbo‐nitrile (6). Both nitriles 5,6 gave in a double cyclization reaction a benzanthrone lactone 12 from which a crystalline derivative of the enol form was isolated, the structure of which was elucidated by 1H‐ and 13C‐nmr spectra. The methylene group of the lactone ring underwent coupling reactions with aromatic diazonium salts to form hydrazone derivatives.
Synthesis of some 2,3‐benzo‐l‐oxaoctems
Authors: Arnoldi Anna , Merlini Lucio , Scaglioni Leonardo 
Published: April 2009

AbstractThe synthesis of some 8‐hydroxy‐2,3‐benzo‐l‐oxaoctems is reported. The imide 7, a potential β‐lactamase inhibitor, was also synthesized.
β‐Angelica lactone epoxide: Chemical behaviour and some synthetic applications
Authors: Ortuño R. M. , Cardellach J. , Font J. 
Published: April 2009

AbstractA new epoxy derivative of ß‐angelica lactone has been synthesized. Its chemical behaviour towards nucleophiles has been explored in order to prepare natural products with a trisubstituted ß‐hydroxy‐γ‐methylbutyrolactone‐type constitution. Thus, some potential precursors have been obtained and an efficient and stereo‐controlled synthesis of (±)‐blastmycinone is reported.
Synthetic approaches to cularines. I. Phenolic oxidative coupling
Authors: De Lera Angel Rodriguez , Saá José M. , Suau Rafael , Castedo Luis 
Published: April 2009

AbstractFerricyanide‐promoted biogenetic‐type phenolic oxidative coupling of an 8,3′‐dihydroxytetrahydrobenzyl‐isoquinoline 19a afforded the isomeric phenolic cularines 5 and 21. Vanadium oxytrifluoride oxidation of the N‐borane complex of 19a afforded, regioselectively, the para‐coupled product 21. Moreover, when this reagent was used on the monophenolic tetrahydrobenzylisoquinoline 19b protected as its N‐borane complex, cularine 1 was regioselectively obtained in good yield. Other structural modifications and reagents were not successful.
A new route to 6‐azachromones. An improved synthesis of 2‐azaxanthone
Authors: Cordonnier Guy , Sliwa Henri 
Published: April 2009

AbstractCondensation of the morpholine enamine of 1‐benzyl‐4‐piperidone with β‐ketoesters yielded 6‐azatetrahy‐drochromones which were debenzylated and aromatized to 6‐azachromones; 2‐azaxanthone has been thus obtained with an improved yield as compared to previous syntheses.
Cyclisation of benzils
Authors: Cremlyn Richard J. , Swinbourne Frederick J. , Shode Olufemi O. , Lynch John 
Published: April 2009

AbstractTreatment of several substituted benzils [3,3′‐ and 4,4′‐dimethyl‐; 2,2′‐, 3,3′‐ and 4,4′‐dichloro‐; 3,3′‐dibromo‐; 4‐(N,N‐dimethylamino)‐] with an excess of chlorosulfonic acid gave the corresponding 3‐chloro‐2‐phenylbenzofuran disulfonyl dichlorides. Disubstitution was confirmed by microanalytical and spectral data for the corresponding bis(N,N‐dimethylaminsulfonamides). The positions of electrophilic substitution were not confirmed with 3,3′‐dimethyl‐, 2,2′‐ and 3,3′‐dichlorobenzils. With 4,4′‐dichlorobenzil, a smaller amount of chlorosulfonic acid enabled the isolation of 3,6,4′‐trichloro‐2‐phenylbenzofuran‐5‐sulfonyl chloride, which was identified by X‐ray analysis of the N,N‐dimethylsulfonamide. The cyclisation failed with 3,3′‐dimethoxy‐, and 3,3′‐ and 4,4′‐dinitrobenzils. The results have been interpreted mechanistically.
New reactions of deoxyvasicinone. Part 6
Authors: Dunn A. D. , Kinnear K. I. , Norrie R. , Ringan N. , Martin D. 
Published: April 2009

AbstractSeveral acylated derivatives of deoxyvasicinone 1 and its analogues were shown to exist as enols. The 3‐hydroxymethyl derivative of 1 was shown to undergo rapid dehydration and products derived from an intermediate 3‐methylene compound were obtained. Novel oxazepino analogues of 1 are reported.
Substituent and solvent effects on tautomeric equilibria of barbituric acid derivatives and isoterically related compounds
Authors: Jovanovic Misa V. , Biehl Edward R. 
Published: April 2009

AbstractN‐Mono and N,N‐dialkyl/diarylbarbituric acids exist in solution as a single tautomer. The 13C nmr spectroscopy shows that they are present in the triketo form in a number of polar and non‐polar solvents. 2‐Thiobarbituric acid derivatives, however, show extensive tautomerization. Their 13C chemical shift assignments were achieved by utilizing models 11a, 11c, 12b and 12d and from which relative tautomer distribution ratios were determined. These ratios were correlated with the dielectric constant of the various solvents (ϵ). Thio‐barbituric acids also formed adducts with solvents having carbonyl groups, characteristic observed only with barbiturates possessing the thione or thiophenolic group. 6‐Amino and 6‐methyluracils and thiouracils exist in DMSO solution as stable “ene” forms as do orotic acid, 24, and its thio analogue 25. Compound 25 undergoes disproportionantion and tautomerization when heated or on prolonged standing in solution. Literature contradictions regarding the structure of “4,6‐dihydroxypyrimidine,” 26, were resolved and its tautomers in solution correctly assigned by 13C nmr.Anions of barbiturics and related systems exist in one of the two possible types A and B, depending on whether ring nitrogens are substituted (type A), or not (type B). Rapid H/D exchange at C5 was evident from C‐deuterium coupling. The redistribution of charge through C4(C6) carbonyl groups shown by 13C shifts of carbonyl carbon atoms of up to 10 ppm as compared to the CO carbons of the neutral species was evident.
Novel heterocyclic systems. Part 26. The synthesis and 13C‐NMR assignment of 1,8‐diazaphenoxathiin
Authors: Lindsy Charles M. , Smith Keith , Martin Gary E. 
Published: April 2009

AbstractAlthough the syntheses of numerous diazaphenoxathiins have been reported, only two dipyrido[1,4]‐oxathiin systems are thus far known, viz. the 1,7‐ and 1,9‐diazaphenoxathiins. The synthesis of a third, 1,8‐diazaphenoxathiin via the condensation of the dianion of 3‐hydroxypyridine‐2(1H)‐thione with 4‐nitro‐3‐chloropyridine 1‐oxide is now described. A minor quantity of 1,7‐diazaphenoxathiin was obtained as a byproduct of the reaction. Complete assignment of the 13C‐nmr spectrum was achieved and this conclusively differentiates the 1,8‐compound from the 1,7‐isomer.
Synthetic applications of 2‐chloro‐3‐formylquinoline
Authors: Srivastava Ranjan Prasad , Neelima  , Bhaduri Amiya Prasad 
Published: April 2009

AbstractNew examples of synthetic applications of 2‐chloro‐3‐formylquinoline, as evident from the novel and facile syntheses of 3‐aminoisooxazolo[5,4‐b]quinoline (4), 3‐hydroxyfuro[2,3‐d]theino[2,3‐b]quinoline‐2‐carboxamide (7) and 3‐hydroxymethyl‐2‐(3‐formyl)phenylquinoline (13), have been furnished.
Reactions of 2‐isocyanatobenzoyl chloride and 2‐carbomethoxyphenyl isocyanate with 5‐aminotetrazole
Authors: Peet Norton P. 
Published: April 2009

AbstractTreatment of 2‐isocyanatobenzoyl chloride (4) with 5‐aminotetrazole (5‐AT) gave 3‐(5‐tetrazolyl)quinazoline‐2,4(1H,3H)‐dione (1) directly. Treatment of 2‐carbomethoxyphenyl isocyanate (5) with 5‐AT gave 2‐[((5‐amino‐1H‐tetrazol‐1‐yl)carbonyl)amino]benzoic acid methyl ester (6) as a kinetic product, which was thermally isomerized to 2‐[((1H‐tetrazol‐5‐ylamino)carbonyl)amino]benzoic acid methyl ester (7), the thermodynamically more stable urea. Cyclization of7with polyphosphoric acid gave 2‐(1H‐tetrazol‐5‐ylamino)‐4H‐3,1‐benzoxazin‐4‐one (2). Urea6was quite labile in solution, as shown by nmr, and readily reacted with methanol to give 2‐[(methoxycarbonyl)amino]benzoic acid methyl ester (10).
Nitriles in organic synthesis: A novel synthesis of benzo[h]pyrimidino[1,2‐c]‐pyridazinone and hydrazonobut‐2‐enonitrile derivatives
Authors: Hafez Ebtisam Abdel Aziz , Kandeel Zaghloul El‐Shahat , Elnagdi Mohamed Hilmy 
Published: April 2009

AbstractA new synthesis of benzo[h]pyrimidino[1,2‐c]pyridazinones via coupling diazotised anthranilic acid with 1‐phenylethylidenemalononitrile (1) is reported. Synthesis of new 1‐antipyrin‐4‐yl and 1‐pyrazol‐5‐ylpyridazine derivatives utilizing 1 as starting material is also described.
The synthesis of monomethoxynaphtho[1′,2′:4,5]thieno[2,3‐c]quinolines
Authors: Pakray Sudabeh , Castle Raymond N. 
Published: April 2009

AbstractA series of monomethoxynaphtho[1′,2′:4,5]thieno[2,3‐c]quinolines has been prepared by photocyclization of the appropriate N‐methoxyphenyl‐1‐chloronaphtho[2,1‐b]thiophene‐2‐carboxamides. Some of the lactams obtained were converted into the thiolactams and their S‐methyl derivatives. The lactams were also converted into the corresponding 6‐chloro derivatives. Some of these were catalytically dechlorinated into the monomethoxynaphtho[1′,2′:4,5]thieno[2,3‐c]quinolines which were then quaternized into the N‐methyl quaternary salts.
Chemistry of the phenoxathiins and isosterically related heterocycles. XXXIII . The influence of intramolecular sulfur‐nitro group interactions on the reactivity at sulfur
Authors: Mehta Mehul U. , Martin Gary E. , Smith Keith 
Published: April 2009

AbstractNitro‐groups positioned ortho to thio‐esters have been shown to engage in strong, non‐bonded intramolecular interactions between the sulfur atom and one of the nitro‐group oxygens. The effect of the sulfur‐nitro group oxygen interaction on the chemical reactivity at the sulfur atom of 9‐nitro‐1‐azaphenoxathiin is reported. Conditions which normally produce the sulfone exclusively have been shown to yield the sulfoxide with only a minimal quantity of the sulfone produced. Protracted periods of reflux are required to produce the sulfone from the sulfoxide.
Synthesis of 2,4′‐dioxospiro[indoline‐3,2′‐thiazolidine]‐5′‐acetic acids: X‐ray structure of 1‐benzyl‐3′‐(4‐chlorophenyl)‐2,4′‐dioxospiro‐ [indoline‐3,2′‐thiazolidine]‐5′‐acetic acid
Authors: Popp Frank D. , Rajopadhye Miland , Brown David S. , Waddington David , Uff Barrie C. 
Published: April 2009

AbstractThe title compounds have been prepared by the cyclocondensation of mercaptosuccinic acid with isatin‐3‐imines. The 1‐benzyl derivatives have been synthesized by simultaneously reacting 1‐benzylisatin, substituted anilines and mercaptosuccinic acid. The structure of the products has been confirmed by X‐ray diffraction measurements.
Application of 1,2,3,5,6,7‐hexahydropyrrolizinium perchlorate in the synthesis of 7a‐substituted hexahydro‐1h‐pyrrolizines
Authors: Miyano Seiji , Yamashita Osamu , Sumoto Kunihiro , Shima Keiyu , Hayashimatsu Mariko , Satoh Fumio 
Published: April 2009

AbstractThe method for preparing 7a‐substituted hexahydro‐1H‐pyrrolizines 2 from 1,2,3,5,6,7‐hexahydropyrrol‐izinium Perchlorate (3) was investigated, by which introduction of a wide variety of functionalities on C(7a) could be achieved easily.
Spirolactones of xanthene. III. Formation and molecular structure of novel spirolactones of xanthene and dibenzo[c,h]xanthene
Authors: Kimura Michio 
Published: April 2009

AbstractThe reaction of 1‐naphthol or phenol derivatives with oxalic and sulfuric acids yielded novel spirolactones. Eight examples (2a‐h) were synthesized by this reaction. The structures of the spirolactones were established from spectral evidence and the X‐ray diffraction studies. Some of the spirolactones form the solvates with the aromatic solvent molecules, such as toluene, xylene and nitrobenzene, and the structure of the nitrobenzene solvate of 2a was determined by the X‐ray analysis.
Reactions of 1‐isopropyl‐3‐methyl‐ and 2,3‐dimethylindoles with triethyl orthoformate: New trisindolylmethanes
Authors: Pindur Ulf , Müller Johann 
Published: April 2009

AbstractIndoles 1 and 2 react with triethyl orthoformate under proton–catalyzed conditions to form trisindolylmethanes. The regioisomer distribution of the products is controlled by steric and electronic factors.
Synthesis of 8‐cyano‐1,4‐dihydro‐4‐oxopyrrolo[1,2‐a]pyrimidine‐3‐carboxylic acids as potential antimicrobial agents
Authors: Abdalla Ghassan M. , Sowell J. Walter 
Published: April 2009

AbstractThe preparation of a variety of 8‐cyano‐1,4‐dihydro‐7‐phenyl‐4‐oxopyrrolo[1,2‐a]pyrimidine‐3‐carboxylicacids and 8‐cyano‐1,4‐dihydro‐7‐p‐fluorophenyl‐4‐oxopyrrolo[1,2‐a]pyrimidine‐3‐carboxylic acids is described.
Intramolecular hydrogen bonding in imidazole‐4(5)‐alkoxycarbonyl‐5(4)‐carboxamide derivatives
Authors: Yasuda Naohiko , Nakamura Asao , Tsuboi Masamichi 
Published: April 2009

AbstractThe ir spectrum of imidazole derivatives, which have an alkoxycarbonyl group and a carboxamide group at the 4‐ and 5‐positions of the imidazole ring respectively, exhibits the shift of the ester carbonyl band to a lower wave number. This phenomenon was investigated by spectroscopic measurements of a group of relevant compounds. The results indicate that the shift is caused by the intramolecular hydrogen bonds between the hydrogen atom of the amide and the carbonyl oxygen of the ester which is enhanced by the resonance stabilization of the imidazole ring.
Synthetic approaches to cularines. II. Ullmann condensation
Authors: De Lera Angel RodrÍGuez , Suau Rafael , Castedo Luis 
Published: April 2009

AbstractThe first total syntheses of O‐methylcularicine 9b and sarcocapnine 9c are described together with a new synthesis of cularine 9a using the Ullmann condensation reaction of the appropriate 2′‐bromo‐8‐hydroxy‐tetrahydrobenzylisoquinoline formed by phase‐transfer alkylation of Reissert compound 2. When this strategy was combined with the lead tetraacetate treatment of the tetrahydrobenzylisoquinoline it yielded 4‐hydroxycularines, from which highly oxidized members of the family can be obtained. This is exemplified by the first synthesis of 4‐hydroxysarcocapnine 19 and its transformation to the 3,4‐dioxoisocularine yagonine 20, rearrangement of which afforded the aristoisocularine aristoyagonine 21.
1,2‐Fused pyrimidines. III. Derivatives of 12H‐pyrido[1′,2′:1,2]pyrimido[4,5‐b]quinoline, a novel heterocyclic system
Authors: Roma G. , Di Braccio M. , Balbi A. , Mazzei M. , Ermili A. 
Published: April 2009

AbstractReactivities of 2‐amino‐4H‐pyrido[1,2‐a]pyrimidin‐4‐ones and 4‐amino‐2H‐pyrido[1,2‐a]pyrimidin‐2‐ones, both N,N‐dialkyl and (N‐alkyl, N‐phenyl)substituted, when treated with the N,N‐dimethylformamide/phosphorus oxychloride Vilsmeier‐Haack reagent XII were compared.Starting from 2‐[(N‐alkyl, N‐phenyl)amino] compounds IXa,b, the expected XVIa,b and XVIIa,b were obtained, which are derivatives of 12H‐pyrido[1′,2′:1,2]pyrimido[4,5‐b]quinoline, a novel heterocyclic system. When 2‐(phenylamino) compound IXc was used a mixture of 3‐formylderivative XVIII and 12H‐pyrido‐[1′,2′:1,2]pyrimido[4,5‐b]quinolin‐12‐one (XIX) resulted from the reaction. On the other hand, 2‐(dialkylamino)‐4H‐pyrido[1,2‐a]pyrimidin‐4‐ones IIIa‐c plainly afforded high yields of 3‐formylderivatives XIVa‐c.In contrast, no significant reaction occurred when 4‐(dialkylamino) and 4‐[(N‐alkyl,N‐phenyl)amino] compounds IIa‐c and VIIIa,b were treated with the reagent XII, under the same as well as more severe conditions. A clear difference in the nucleophilic reactivity of C‐3 position between these two classes of isomers is pointed out by the above summarized results.
Polycyclic N‐hetero compounds. XXIX. Synthesis and antidepressive evaluation of 15‐thia‐11,13‐diazasteroidal analogues and their precursors
Authors: Hirota Takashi , Hamazaki Rieko , Ohdoi Takako , Sasaki Kenji , Namba Tetsuto 
Published: April 2009

AbstractSyntheses of novel 15‐thia‐11,13‐diazasteroidal skeleton IV and its D‐homo analogues are described. Meso‐ionic derivatives of IV were also synthesized. Antidepressive activities of these compounds and their precursors were screened. D‐Dihomothiadiazasteroid IX and 3,4,5,6‐tetrahydrobenzo[h]quinazoline‐4‐thione (V) exhibited antireserpine action.
Synthesis and antimalarial activity of a series of 2,4‐diamino‐6‐[(N‐alkylanilino)methyl]quinazolines
Authors: Werbel Leslie M. , Elslager Edward F. , Newton Linda S. 
Published: April 2009

AbstractA series of 2,4‐diamino‐6‐[(N‐alkylanilino)methyl]quinazolines were prepared by bromination of 2,4‐dibenz‐amido‐6‐methylquinazoline followed by treatment with secondary arylamines and deblocking with base. A variety of analogs demonstrated substantial activity against Plasmodium berghei infections in mice.
A convenient synthesis of nicotinate esters from 3‐cyanopyridones
Authors: Paine John B. 
Published: April 2009

AbstractA convenient synthesis of alkyl‐substituted ethyl nicotinates 8 was devised, using 3‐cyano‐2(1H)‐pyridones 4. These were converted to the corresponding 2‐bromo‐3‐cyanopyridines 5 with boiling phosphorus tribromide. The resulting 5 were smoothly debrominated to 3‐cyanopyridines 6 with zinc dust in boiling ethanolic acetic acid. The nitrile function was hydrolyzed in boiling 6N hydrochloric acid, and the resulting nicotinic acid hydrochlorides 7 esterified with refluxing triethyl orthoformate, to give the ethyl nicotinates 8. A modified formylation of 2‐butanone led to the sodium salt of 2‐methyl‐3‐oxobutanal (3a) of enhanced purity.
17O NMR Investigation of cyclic aromatic ethers
Authors: Boykin David W. , Martin Gary E. 
Published: April 2009

AbstractA linear relationship between the C‐O‐C angle and the molecular dihedral angle in a series of phenoxathi‐ins and azaphenoxathiins is reported. 17O nmr spectroscopic data (natural abundance in acetonitrile at 75°C) were obtained on eight cyclic aromatic ethers 1‐8, including phenoxathiins, and two model compounds, acyclic aromatic ethers 9 and 10. The chemical shifts of the cyclic aromatic ethers were very sensitive to structural variations and were dependent upon electonic and conformational effects; however, no quantitative relationship between 17O chemical shift and geometric parameters was found.
Synthesis of 1,2‐di‐(4‐pyridyl)ethylenediamine and related compounds
Authors: Braña Miguel F. , Castellano José M. , Rodriguez Maria L. López , Gálvez Magdalena , Amil Manuel R. , Rubio Enrique 
Published: April 2009

AbstractHydrolysis of N,N'‐diacyl‐1,2‐di(4‐pyridyl)ethylenediamines 1 in aqueous sulfuric acid gave the corresponding imidazolines 3. 1,2‐Di‐(4‐pyridyl)ethylenediamine 2 was prepared in 61 % yield by treating N,N'‐di‐t‐butyl‐oxycarbonyl‐1,2‐di(4‐pyridyl)ethylenediamine 4 with trifluoroacetic acid or in 94% yield by the hydrolysis under basic conditions of N,N'‐diphthaloylglycyl‐1,2‐di(4‐pyridy)ethylenediamine 13.
Furopyridines. VII. Preparation and hydrolysis of 2‐cyano and 3‐cyano derivatives of furo[3,2‐b]‐, furo[2,3‐c]‐ and furo[3,2‐c]pyridine
Authors: Morita Hiroyuki , Shiotani Shunsaku 
Published: April 2009

AbstractThis paper describes the preparation and hydrolysis of 2‐cyano and 3‐cyano derivatives of furo[3,2‐b]‐, furo[2,3‐c]‐ and furo[3,2‐c]pyridine. Treatment of furopyridines 1a, 1b and 1c with n‐butyllithium in hexane‐tetrahydrofuran at ‐70° and subsequent addition of N,N‐dimethylformamide yielded 2‐formyl derivatives 2a, 2b and 2c. Dehydration of the oximes 4a, 4b and 4c of 2a, 2b and 2c gave 2‐cyano compounds 5a, 5b and 5c, which were hydrolyzed to give 2‐carboxylic acids, 6a, 6b and 6c, respectively. Reaction of 3‐bromo compounds 7a, 7b and 7c with copper(I) cyanide in N,N‐dimethylformamide afforded 3‐cyano derivatives 8a, 8b and 8c. Alkaline hydrolysis of 8a, 8b and 8c gave compounds formed by fission of the 1‐2 bond of furopyridines 9a, 9b and 9c, while acidic hydrolysis gave the corresponding carboxamides, 10a, 10b and 10c.
Synthesis of novel 4‐amino‐1,4‐benzodiazepine‐2,5‐diones for anticonvulsant testing
Authors: Tita Terence T. , Kornet Milton J. 
Published: April 2009

AbstractA series of novel 4‐amino‐1,4‐benzodiazepine‐2,5‐diones was synthesized via two pathways. The first method involved reductive alkylation of unsymmetrical hydrazines with glyoxylic acid, followed by Fisher esterification. The resulting N‐aminoglycinate ethyl ester was subsequently o‐nitrobenzoylated, reduced, and thermally cyclized to obtain 4‐dialkylaminobenzodiazepinones. In the second method methylhydrazine was acetylated at Nα then benzoylated at Nβ to give 1,2‐diacylhydrazines. Alkylation with ethyl bromoacetate and reduction of the nitro group, followed by thermal cyclization yielded 4‐acetamidobenzodiazepinones. All title compounds were evaluated in mice in MES seizure and sc Met seizure threshold tests for anticonvulsant activity, and in the rotorod test for neurotoxicity. Activity and toxicity were both minimal.
On the mechanism of hydrolysis of the triazolobenzodiazepine, triazolam. Spectroscopic study
Authors: Jiménez R. M. , Domínguez E. , Badía D. , Alonso R. M. , Vicente F. , Hernández L. 
Published: April 2009

AbstractThe hydrolysis of 8‐chloro‐6‐(2′‐chlorophenyl)‐1‐methyl‐4H[1,2,4]triazolo[4,3‐a][1,4]benzodiazepine (Triazolam) at room temperature, involves a reversible mechanism. The intermediate is a protonated species and the final product is the ring‐opened compound resulting from the reversible scission of the imine bond. The two compounds were determined simultaneously as a function of pH with pmr and cmr spectrometry. Spectral data of the benzophenone derivative II (ir, cmr, pmr) are reported.
Synthesis of 3‐amino‐5H‐pyrimido[5,4‐b]indol‐4‐one derivatives
Authors: Monge A. , Palop J. A. , Parrado P. , Perez‐Ilzarbe C. , Fernández‐Alvarez E. 
Published: April 2009

AbstractStarting with ethyl 3‐aminoindole‐2‐carboxylate, the synthesis of 3‐amino‐5H‐pyrimido[5,4‐b]indole‐2,4‐dione 5, 3‐amino‐5H‐pyrimido[5,4‐b]indol‐4‐one 10 and some related compounds is described. Preliminary results about the inhibition of platelet aggregation by these compounds is reported.