bluuebunny/crossref_metadata_2025_split huggingface dataset:
Diazines. IX. Metalation of 2‐chloro, 2‐methoxy and 2‐pivaloylaminoquinoxaline
Authors: Turck A. , Ple N. , Tallon V. , Queguiner G. 
Published: March 2009

AbstractThe lithiation of 2‐chloro, 2‐methoxy and 2‐pivaloylaminoquinoxaline was studied. In the case of 2‐chloro and 2‐methoxyquinoxaline the simultaneous formation of dimers could not be avoided. The resulting lithio derivatives were reacted with carbonyl compounds and iodine. Yields in excess of 50% were obtained.
Pyridine and pyrimidine ring syntheses from 4‐(4‐morpholino)‐3‐pentenone and from ethyl 3‐(4‐morpholino)‐2‐butenoate
Authors: Ratemi Elaref S. , Namdev Nivedita , Gibson Martin S. 
Published: March 2009

Abstract3‐Substituted 2(1H)‐pyridones are produced from reaction of 4‐(4‐morpholino)‐3‐pentenone 1 with each of the following carbon acids: cyanoacetamide, malononitrile, cyanothioacetamide, acetylacetamide, benzoyl‐acetonitrile. Reaction of ethyl 3‐(4‐morpholino)‐2‐butenoate 2 with cyanoacetamide gives the corresponding hydroxypyridone. Pyrimidines are formed by reaction of 1 and of 2 with benzamidine and with S‐benzylthio‐urea; in the last case, the eliminated morpholine displaces the benzylthio group to give the final product.
Pyridazines. LXVIII. Convenient Synthesis of Phenyl (6‐Substituted 3‐Pyridazinyl) Ketones via the Oxidative Decyanation Route
Authors: Heinisch Gottfried , Langer Thierry 
Published: March 2009

AbstractA convenient approach to aryl 3‐pyridazinyl ketones 4, 7‐10 bearing various O‐, N‐, or C‐substituents at C‐6 of the diazine nucleus via oxidative decyanation of appropriate aryl‐heteroaryl‐acetonitriles is proposed.
Recognition by a new chiral dimethyl‐substituted phenanthrolino‐18‐crown‐6 diester ligand of the enantiomers of various organic ammonium perchlorates
Authors: Wang Tingmin , Bradshaw Jerald S. , Huszthy Peter , Kou Xiaolan , Dalley N. Kent , Izatt Reed M. 
Published: March 2009

AbstractTwo new chiral dimethyl‐substituted phenanthrolino‐18‐crown‐6 diester ligands [(S,S)‐3] and [(S,S)‐4] (see Figure 1) were prepared through the reactions of 1, 10‐phenanthroline‐2,9‐dicarboxylyl dichloride with (S,S)‐dimethyl‐substituted tricthylene glycol and (S,S)‐dimethyl‐substituted benzotricthylene glycol, respectively. The complexation of (S,S)‐3 with the enantiomers of various organic ammonium perchlorates in various solvent systems was studied by 1H nmr spectral techniques and molecular mechanics. The degree of enantiomeric recognition was determined by the difference in the free energy of activation values (ΔΔG‡C) and the difference in log K values for these interactions. The extensive π system in the ligand plays an important role for the strong interaction and recognition. The 1H nmr NOESY spectra and molecular mechanics calculations for the interactions of the new ligand with the organic ammonium salts further proved the existence of a π‐π interaction.
A novel synthesis of pyrido[2,3‐b][1,5]benzodiazepines
Authors: Okamoto Yoshihisa , Kurasawa Yoshihisa , Aotsuka Tomoji 
Published: March 2009

AbstractA novel and convenient synthesis of the title compounds 4, 5, 11, and 13 is described, involving the ring transformation of 1,5‐benzodiazepine derivatives 1a and 1b with active methylene compounds.
The reaction of aromatic α,β‐unsaturated ketones with 4,5‐diamino‐1,6‐dihydropyrimidin‐6‐ones
Authors: Insuasty Braulio , Ramos MÓNica , Quiroga Jairo , Sanchez Adolfo , Nogueras Manuel , Hanold Norbert , Meier Herbert 
Published: March 2009

AbstractThe reaction of 4,5‐diamino‐1,6‐dihydropyrimidin‐6‐ones 1 with one equivalent of the chalcones 2 leads in an acidic medium to the formation of the 2,4‐diaryl‐2,3,6,7‐tetrahydro‐1H‐pyrimido[4,5‐b][1,4]diazepin‐6‐ones 3a‐m. The structure elucidation of the products is based on detailed nmr investigations including selective 13C[1H] decoupling experiments.
Synthesis and biological activity of novel mitomycin C analogs derived from mitomycin A
Authors: Kuroda Tokuyuki , Hisamura Koji , Matsukuma Ikuo , Osawa Yutaka , Sugaya Toru , Nishikawa Hiroshi , Morimoto Makoto , Ashizawa Tadashi , Nakamizo Nobuhiro , Otsuji Yoshio 
Published: March 2009

AbstractA variety of mitomycin C analogs were synthesized from mitomycin A and their biological activities were studied. Mitomycin A (1) underwent nucleophilic displacement reactions involving intramolecular hydrogen migrations upon treatment with nitrogen nucleophiles bearing mobile hydrogens, but the mode of hydrogen migration depended on the nature of the nucleophiles. The reaction with alkoxyamines gave compounds 6 and 7 which have the 5H‐6‐alkoxyimino‐4,7‐dione structure in ring A of 1. However, the reaction with hydroxylamine and benzoylhydrazine afforded compounds 11 and 13 which have the 4‐hydroxy‐6‐hydroxyimino‐7‐one structure and the 4‐hydroxy‐6‐hydrazono‐7‐one structure, respectively, in ring A of 1. These products were converted into various types of mitomycin C derivatives by methylation with methyl iodide or dimethyl sulfate. The mechanistic features of these reactions are discussed. The in vitro and in vivo biological activities were tested by using P388 leukemia and Sarcoma 180 tumor cells. Several of the synthesized compounds exhibited better activity than that of mitomycin C.
NMR study on the tautomeric equilibria between the hydrazone imine and diazenyl enamine forms in side chained quinoxalines: Solvent effects and temperature dependence
Authors: Kurasawa Yoshihisa , Ishikura Aiko , Ikeda Kazue , Hosaka Tomoyoshi , Matsumoto Yuko , Takada Atsushi , Kim Ho Sik , Okamoto Yoshihisa 
Published: March 2009

AbstractThe reaction of 7‐chloro‐4‐ethoxycarbonylmethylene‐4,5‐dihydro‐1,2,4‐triazolo[4,3‐a]quinoxaline 6 with 4‐ethoxycarbonyl‐1‐methyl‐1H‐pyrazole‐5‐diazonium chloride or 4‐cyano‐1,3‐dimethyl‐1H‐pyrazole‐5‐diazonium chloride gave 7‐chloro‐4‐[α‐(4‐ethoxycarbonyl‐1‐methyl‐1H‐pyrazol‐5‐ylhydrazono)‐ethoxycarbonylmethyl]‐1,2,4‐triazolo[4,3‐a]quinoxaline 8a or 7‐chloro‐4‐[α‐(4‐cyano‐1,3‐dimethyl‐1H‐pyrazol‐5‐ylhydrazono)ethoxycarbonylmethyl]‐1,2,4‐triazolo[4,3‐a]quinoxaline 8b, respectively, while the reaction of 7‐chloro‐4‐ethoxycarbonylmethylene‐4,5‐dihydrotetrazolo[1,5‐a]quinoxaline 7 with 4‐ethoxycarbonyl‐1‐methyl‐1H‐pyrazole‐5‐diazonium chloride or 4‐cyano‐1,3‐dimethyl‐1H‐pyrazole‐5‐diazomum chloride provided 7‐chloro‐4‐[α‐(4‐ethoxycarbonyl‐1‐methyl‐1H‐pyrazol‐5‐ylhydrazono)ethoxycarbonylmethyl]tetrazolo[1,5‐a]quinoxaline 9a or 7‐chloro‐4‐[α‐(4‐cyano‐1,3‐dimethyl‐1H‐pyrazol‐5‐ylhydrazono)ethoxycarbonylmethyl]tetrazolo[1,5‐a]quinoxaline 9b, respectively. Compounds 8a,b and 9a,b showed the tautomeric equilibria between the hydrazone imine C and diazenyl enamine D forms in dimethyl sulfoxide and/or trifluoroacetic acid, and the effects of solvent and temperature on the tautomer ratios of C to D were studied by the nmr measurements in a series of mixed trifluoroacetic acid/dimethyl sulfoxide media (compounds 8a,b and 9a,b) and at various temperatures (compounds 8a,b).
A simple, efficient, two‐step synthesis of symmetric 2,7‐dialkyl‐1,6‐dioxaspiro[4.4]nonanes
Authors: Ballini Roberto , Bosica Giovanna , Uselli Alessandra 
Published: March 2009

AbstractA two‐step synthesis of symmetric 2,7‐dialkyl‐1,6‐dioxaspiro[4.4]nonanes has been achieved by double Michael addition of nitromethane with two moles of enones on Amberlyst A21, followed by in situ reduction with sodium borohydride, then spontaneous spiroketalization of the obtained nitrodiol, by the Nef reaction under acidic conditions, affords the title compounds in good yields.
Ring transformations of heterocyclic compounds. IX. Trifluoromethyl Substituted 2‐Amino‐3,4,6‐triarylbenzophenones by Ring Transformation of 2,4,6‐Triarylpyrylium Salts with Trifluoromethylbenzyl Cyanides
Authors: Zimmermann Thomas 
Published: March 2009

AbstractThe preparation of hitherto unknown trifluoromethyl substituted 2‐amino‐3,4,6‐triarylbenzophenones 3 by a 2,5‐[C4+C2] rins transformation of 2,4,6‐triarylpyrylium salts 1 with trifluoromethylbenzyl cyanides 2 in the presence of sodium methanolate in methanol is reported. Spectroscopic data of the benzophenones 3 and the mode of their formation are discussed.
1,3,4,6‐Tetrakis(isopropylthio)thieno[3,4‐c]thiophenium bis(tetrafluoroborate): X‐ray crystal structure of a stable thieno[3,4‐c]thiophene dication
Authors: Tsubouchi Akira , Inoue Hiroo , Yanagi Kazunori 
Published: March 2009

AbstractThe structure of the 1,3,4,6‐tetrakis(isopropylthio)thieno[3,4‐c]thiophene dication (2) prepared from 1,3,4,6‐tetrakis(isopropylthio)thieno[3,4‐c]thiophene (1) by two‐electron oxidation was investigated by X‐ray crystallographic analysis. The results revealed that the positive charges are largely delocalized on the two i‐PrS‐C‐C‐C‐SPr‐i moieties.
Research on nitrogen and sulfur heterocyclic compounds: Synthesis of 10H‐pyrrolo[1,2‐a]thieno[3,4‐e][1,4]‐diazepin‐5(4H)‐one and some derivatives
Authors: Daich Abdelali , Morel Jean , Decroix Bernard 
Published: March 2009

AbstractThe synthesis of 10H‐pyrrolo[1,2‐a]thieno[3,4‐e][1,4]diazepin‐5(4H)‐one (16) and some derivatives are described from methyl 3‐bromomethylthiophene‐4‐carboxylate (5). The key step of these sequences is the intramolecular cyclization of the carbonylazides 12 and 13.
Intramolecular photoreactions of 6‐(ω‐alkenyl)‐4‐methoxy‐2‐pyrones
Authors: Shimo Tetsuro , Matsuzaki Shigeki , Somekawa Kenichi 
Published: March 2009

Abstract6‐(ω‐Alkenyl)‐2‐pyrones 3a‐c and 8a, b were prepared and the photochemical reactions were investigated. Photosensitized reactions of 3b, c gave intramolecular [2+2]‐cycloadducts 11b, c as tricyclic lactones, site‐and regio‐specifically. They are not frontier‐orbital‐controlled adducts. On the other hand, 3a, 8a, b afforded cyclobutenecarboxylic acids, 10a, 14a, b, respectively. The end‐ester group at the side‐chain is thought not to be effective for the intramolecular phptoaddition.
Substituent effects on the tautomer ratios between the hydrazone imine and diazenyl enamine forms in side‐chained quinoxalines
Authors: Kurasawa Yoshihisa , Hosaka Tomoyoshi , Ikeda Kazue , Matsumoto Yuko , Ishikura Aiko , Takada Atsushi , Kim Ho Sik , Okamoto Yoshihisa 
Published: March 2009

AbstractThe 3‐(arylhydrazono)methyl‐2‐oxo‐1,2‐dihydroquinoxalines 9–11 were synthesized by the reaction of the quinoxalines 6–8 with various p‐substituted benzenediazonium salts. Compounds 9–11 showed the tautomeric equilibria between the hydrazone imine A and diazenyl enamine B forms in dimethyl sulfoxide media. The substituent effect on the tautomer ratios of A to B was studied by the nmr spectroscopy to clarify that the presence of the ester group R2 on the hydrazone carbon and electron‐donating p‐substituent R1 on the side chain benzene ring exhibited a tendency to increase the ratios of the tautomer A.
Facile synthesis of novel spiro[azetidine‐2,4′(1′H)‐isoquinoline‐1′,3′,4(2′H)‐triones]
Authors: Malamas Michael S. 
Published: March 2009

AbstractA convenient general method for the synthesis of a new heterocycle, spiro[azetidine‐2,4′(1′H)‐iso‐quinoline‐1′,3′,4(2′H)‐trione] is described. The key intermediate 2 was prepared by direct halogenation of position‐4 of acid 3 with thionyl chloride, and subsequent treatment of the generated 4‐Cl, 4‐acetyl chloride 11 with a THF/NH3 solution at low temperature.
A novel synthesis of 6,7,8,9‐tetrahydro‐5H‐dibenzo[c,g]carbazole
Authors: Dimmock J. R. , Pandeya S. N. , Puthucode R. N. , Quail J. W. 
Published: March 2009

AbstractThe synthesis of the title compound from 2‐tetralone and thiosemicarbazide is reported. The structure was obtained by X‐ray crystallography and its evaluation in certain anticonvulsant, cytotoxic and DNA binding screens is described.
The syntheses and NMR spectra of the twelve isomeric thieno[b]fused naphthyridines
Authors: Björk Patrick , Hörnfeldt Anna‐Britta , Gronowitz Salo 
Published: March 2009

AbstractThrough the use of Pd(0)‐catalyzed couplings between 2‐(2‐trimethylstannyl‐3‐pyridyl)‐1,3‐dioxolane, 3‐trimethylstannyl‐2‐pyridine carboxaldehyde, 3‐trimethylstannyl‐4‐pyridine carboxaldehyde and 4‐trimethyl‐stannyl‐3‐pyridine carboxaldehyde with t‐butyl‐N‐(3‐bromo‐2‐thienyl)carbamate, t‐butyl‐N‐(2‐bromo‐3‐thienyl)carbamate and t‐butyl‐N‐(4‐bromo‐3‐thienyl)carbamate in N,N‐dimethylformamide at 100°, using cupric oxide as a coreagent, all twelve isomeric thieno[b]naphthyridines have been synthesized in an one‐pot procedure. A detailed study of the 1H and 13C nmr spectra of these isomers has been undertaken.
Studies on pyrazines. 29. High regioselective synthesis of chloropyrazines from 3‐substituted pyrazine 1‐oxides
Authors: Sato Nobuhiro , Fujii Megumi 
Published: March 2009

AbstractReaction of 3‐methoxy‐ or 3‐chloropyrazine 1‐oxides with refluxing phosphoryl chloride in the presence of amine led to a high regioselective formation of 3‐substituted 2‐chloropyrazines. In contrast, the use of chloroacetyl chloride instead of phosphoryl chloride enabled different regioselectivity to yield 6‐substituted 2‐chloropyrazines, particularly 3‐methoxycarbonylpyrazine 1‐oxide was almost exclusively converted into methyl 6‐chloropyrazinecarboxylate under the conditions without the amine.
Total assignment of the 1H and 13C NMR spectra of pyrrolizino‐[3,4,5‐a,b]isoquinoline, benzo[1,2]pyrrolizino[3,4,5‐a,b]isoquinoline and 2‐methylthiopyrrolizino[3,4,5‐a,b]isoquinoline
Authors: Castle Lyle W. , Tominaga Yoshinori , Castle Raymond N. 
Published: March 2009

AbstractThe total 1H and 13C nmr spectral assignments of pyrrolizino[3,4,5‐a,b]isoquinoline, benzo‐[1,2]pyrrolizino[3,4,5‐a,b]isoquinoline and 2‐methylthiopyrrolizino[3,4,5‐a,b]isoquinoline are reported. The concerted use of the COSY, HMQC, HMBC and nOe‐difference experiments is used to generate total assignments of the 1H and 13C nmr spectra.
Synthesis of tetrahydroimidazo[1,5‐b]‐β‐carboline derivatives with complex basic substituents
Authors: De Miguel Pilar , Martín Nazario , Braña Miguel F. 
Published: March 2009

AbstractNovel tetrahydroimidazo[1,5‐b]‐β‐carbolines derivatives 6 bearing complex basic chains as substituents on the imidic nitrogen have been prepared in a one‐pot reaction. This simple experimental procedure overcomes the direct handle of isocyanates which can be favorably generated “in situ” from carbonyldiimidazole (CDI) and different amines. The stereochemistry of the novel compounds was determined by nmr experiments.
Isoxazolium enolates derived from α,β‐unsaturated and 1,3‐dicarbonyl compounds. The through‐space effect of the enolate moiety on the chemical shift of α‐protons
Authors: Zvilichovsky Gury , Gurvich Vadim 
Published: March 2009

AbstractThe reaction of 4‐phenyl‐3,5‐dihydroxyisoxazole with α,β‐unsaturated cyclic ketones and 1,3‐cyclic diketones was studied. β‐Substituted α,β‐unsaturated ketones give pairs of isomeric isoxazolium enolates. The remarkable influence of the heterocyclic betaine on the proton chemical shifts is discussed. 1,3‐Cyclic diketones reacted spontaneously with 4‐phenyl‐3,5‐dihydroxyisoxazole yielding isoxazolium enolate enols and enol ethers.
New proton‐ionizable macrocyclic compounds containing one and two triazole subcyclic units — synthesis and complexation properties
Authors: Elshani Sadik , Apgar Pete , Wang Shaofen , Wai C. M. 
Published: March 2009

AbstractA series of new macrocyclic compounds containing one and two proton‐ionizable triazole subcyclic units have been prepared and characterized. These triazolo‐crowns containing benzo, tert‐butylbenzo or cyclohexano lipophilic groups show varying solubilities in chloroform. The bistriazolo‐crowns dissolved in chloroform are highly effective for extraction of lead, mercury, and gold from aqueous solutions.
Reactions of donor‐substituted furans with electrophilic ethylenes
Authors: Mloston Grzegorz , Huisgen Rolf 
Published: March 2009

Abstract2‐Methoxyfuran and 2‐p‐tolyloxyfuran were attacked at the 5‐position by tetracyanoethylene or the super‐electrophilic 2,2‐bis(trifluoromethyl)ethylene‐1,1‐dicarbonitrile affording (Z)‐3‐cyclopropylacrylic esters, substituted in the 3‐membered ring. Initially formed zwitterions undergo simultaneous opening of the furan and closure of the cyclopropane ring. In the presence of pyridine, 1,3‐prototropy converts the zwitterion to 5‐substitution products of the furans.
Cobalt(I)‐catalyzed cocyclotrimerization of acetylene with 2,6‐dicyanopyridines
Authors: Chelucci Giorgio , Cabras M. Antonietta , Saba A. 
Published: March 2009

AbstractA procedure of general application to the synthesis of alkyl‐substituted 2‐cyano‐6‐(2‐pyridyl)pyridines from alkylpyridines is outlined.
Direct monobromination of substituted 4‐oxoquinoline‐3‐carboxylic acid derivatives
Authors: Moẑek Irena , Ŝket Boris 
Published: March 2009

AbstractN‐Bromosaccharin in the presence of pyridinium poly(hydrogen fluoride) can be used for monobromination of ethyl esters of 6‐ and 7‐substituted‐4‐oxo‐1,4‐dihydroquinoline‐3‐carboxylic acids. The reactions take place at the C6 or C8 positions, depending on the types and positions of the substituents.
Synthesis and NMR studies of thiazolidine‐4‐carboxylic acid derivatives containing a nitro ester function
Authors: Benedini Francesca , Ferrario Francesco , Sala Alberto , Sala Luca , Soresinetti Pier Angelo 
Published: March 2009

AbstractThe preparation of thiazolidine‐4‐carboxylic acid derivatives containing a 2‐nitrooxyethylamine group, potentially active as vasodilators, is reported. Their1H nmr studies carried out to establish the configuration of the C2 stereocenter and the full assignment of their1H and13C nmr spectra, are also reported.
Synthesis of 5H‐[1]benzopyrano[4,3‐b]pyridin‐5‐ones containing an azacannabinoidal structure
Authors: Heber D. , Berghaus Th. 
Published: March 2009

AbstractStarting from 7‐alkoxy‐4‐aminocoumarins 5,6,8,12, and 13 as key intermediates, this paper describes two different methods for the preparation of azacannabinoidal 5H[1]benzopyrano[4,3‐b]pyridin‐5‐ones 24–27, 38, and 39 containing typical structural requirements for ZNS activity. First, Michael addition of 6 and 8 to the double bonds of alkyl vinyl ketones 14 and 15 resulted in a mixture of tetrahydropyridines 24–27 and fused pyridines 20–23 the latter of which were reduced by sodium cyanoborohydride to give the target compounds 24–27. The second, pyridine ring closure was accomplished by a combination of Vilsmeier acetylation and formylation resulting in fused 4‐chloropyridines 31–33 followed by reduction.
Experimental and computational studies of trifluoromethylation of aromatic amines by the system trifluoroiodomethane‐zinc‐sulfur dioxide
Authors: Strekowski Lucjan , Hojjat Maryam , Patterson Steven E. , Kiselyov Alexander S. 
Published: March 2009

AbstractSeveral trifluoromethyl‐substituted aromatic and heteroaromatic amines have been obtained by the reactions of the corresponding amines with the title reagent system. Computational results provide rationalization for the observed regioselectivities and support a mechanism in which the electrophilic trifluoromethyl radicals interact with the aromatic ring at the sites with the greatest electron density of the HOMO orbitals, and then the resultant adducts are oxidized to cations. The products obtained are potential building blocks for a number of heterocyclic systems.
Novel heterocycles derived from 3‐acyloxy‐ and 3‐acetamidoquinuclidines
Authors: Besidsky Yevgeny , Luthman Kristina , Hacksell Uli 
Published: March 2009

AbstractNew quinuclidine derivatives with 3‐spiro annelated oxathioline, furanone, and pyrrolinone heterocycles have been synthesized from 3‐mesyloxy‐, 3‐acetoxy‐, and 3‐acetamidoquinuclidine‐3‐carbonitrile, respectively, by treatment with base. Treatment of 3‐acetamidoquinuclidine‐3‐carbonitrile (3) with potassium hydride resulted in decyanation whereas alkyllithium reagents attacked the cyano group in 3 to produce the corresponding imines. Oxidative cyclization of the N‐benzylated derivative of 3 with palladium acetate gave the tetracyclic compound 5‐acetyl‐1,4‐ethano‐1,2,3,4,5,6‐hexahydrobenzo[c]‐1,5‐naphthyridine.
Reaction of oxalyl and malonyl chloride with 1,1‐dimethyl‐2‐substituted hydrazides
Authors: Sarker S. R. , Stone D. M. , Evain E. J. , Cooley J. H. , Scott B. L. , Willett R. D. 
Published: March 2009

AbstractRecently we reported the reaction of 1,1‐dimethyl‐4‐substituted semicarbazides with phosgene to occur with formation of several new heterocyclic ring systems. Here we report the reaction of several semicarbazides, thiosemicarbazides and related acyl substituted hydrazides with oxalyl chloride and malonyl chloride. These reactions occur with the formation of heterocyclic products which are oxadiazolinones, imidazolidinetriones, 2‐thioxoimidazolindine‐4,5‐diones, and 2‐thioxo‐1,3‐diazine‐4,6‐diones (2‐thioxopyrimidine‐4,6‐diones).
Structural study of 5‐methoxyfuro[3,2‐e]imidazo[1,2‐c]pyrimidine
Authors: Quijano M. Luisa , Nogueras M. , Sánchez A. , Melgarejo M. , López R. , Jimeno M. Luisa , Low J. N. , Howie R. A. , Ferguson G. 
Published: March 2009

AbstractThe nmr and X‐ray diffraction data of the novel ring system furo[3,2‐e]imidazo[1,2‐c]pyrimidine are reported in this paper. The crystal and molecular structure of this compound (C9H7N3O2·1/2H2O) has been solved at room temperature. Crystals are monoclinic in a space group of P2/n with cell constants a = 9.982(8), b = 13.526(9) and c = 13.981(9) Å, β = 107.44(5)°, V = 1800.9 Å3, Z = 8, Dx = 1.462 Mg·m−3. The structure was solved by full matrix least square refinement giving a final R = 0.054 (Rw = 0.069) for 1263 reflections (I>3.0σ(I)). The compound is essentially planar, existing in two slightly structural different forms, A and B. These are held in pairs with symmetry related molecules by hydrogen bonds formed with two water molecules. Then the dimeric units are stacked parallel to the c axis to form the tridimensional packing.
Synthesis of 3‐alkyl‐8‐substituted‐ and 4‐hydroxy‐8‐substituted‐2,3,4,5‐tetrahydro‐1H‐2‐benzazepines
Authors: Grunewald Gary L. , Dahanukar Vilas H. 
Published: March 2009

AbstractBased on the Schmidt reaction and an iodolactone ring expansion reaction, two different synthetic routes to substituted 2,3,4,5‐tetrahydro‐1H‐2‐benzazepines were developed. The Schmidt reaction on 2,3‐dihydro‐2H‐1‐naphthalenone (1) gave 3, the product resulting from the alkyl group migration, as the major product instead of the tetrazole 2. This prompted the investigation of the Schmidt reaction on aromatic ketones 8 and 12. The product 9 due to alkyl group migration was the major product of the Schmidt reaction on 2‐methyl‐3,4‐dihydro‐2H‐1‐naphthalenone (8). The β‐keto diester 12 gave a mixture of decarb‐oxylated lactams after the Schmidt reaction. In this case, the lactam 13 resulting from the migration of the aromatic ring dominated over the other lactam 14. When lactam 14 was subjected to nitration, a single regioisomer was produced and transformed to the bromo alcohol 19. The other approach was based on the single pot ring expansion of the iodolactone 22 to the lactam 23 in the presence of methanolic ammonia. The iodolactone 22 was readily prepared from 2‐allylbenzoic acid.
The photochemical reactions of the halogenated N‐benzylanilines. Mechanism of the reactions
Authors: Park Yong‐Tae , Lee Ick‐Hyung , Kim Young‐Hee 
Published: March 2009

AbstractSeveral N‐(2‐halobenzyl)anilines and N‐benzyl‐2‐haloanilines have been synthesized and their photochemical reactions studied. Upon irradiation, the aqueous acetonitrile solution of N‐benzyl‐2‐chloroaniline was cyclized and reduced to give phenanthridine, 5,5′,6,6′‐tetrahydro‐6,6′‐biphenanthridyl (THBP), N‐ben‐zylaniline, and bibenzyl. Similar products were produced in the photochemical reactions of other halo‐genated N‐benzylanilines, except iodo‐substituted N‐benzylanilines. No dimer (THBP) was produced from the iodo‐substituted N‐benzylanilines. Both singlet and triplet states are involved in the photochemical reactions of the haloarenes.
Syntheses of 1,5,6‐trimethyl‐2‐aminoimidazo[4,5‐b]pyridine and 3,5,6‐trimethyl‐2‐aminoimidazo[4,5‐b]pyridine
Authors: Tanga M. J. , Bupp J. E. , Tochimoto T. K. 
Published: March 2009

AbstractTwo potential mutagens found in food, 1,5,6‐trimethyl‐2‐aminoimidazo[4,5‐b]pyridine and 3,5,6‐trimethyl‐2‐aminoimidazo[4,5‐b]pyridine, are synthesized.