bluuebunny/crossref_metadata_2025_split huggingface dataset:
Synthesis of artificial receptors as potential candidates for recognition and binding of pterin analogs
Authors: Papadopoulou Maria V. , Goswami Shyamaprosad , Hamilton Andrew D. 
Published: March 2009

AbstractOpen chain podands 2a‐c and macrocycles 2d‐e have been synthesized as potential candidates for 4‐aminopterin recognition and binding, featuring Hbonding characteristics and “stacking interaction” 2e. Preliminary binding studies between 6, 7, and 8 (simpler analogs of the above 2a‐e) as “bosts” and appropriate “guests”, showed that carbamates 2a and 2e are the most promising receptors for 4‐aminopterin binding.
Acetylenic amides. 2. The generation and reactions of dianions derived from 2‐propynamides
Authors: Coppola Gary M. , Damon Robert E. 
Published: March 2009

AbstractThe dianion of N‐benzyl‐2‐propynamide can be generated by the treatment of 4 with two equivalents of LDA at −65° or ethylmagnesium bromide at −20°. The trilithio species 6 is readily formed using 3 equivalents of LDA. Reaction of 5 with aldehydes or ketones produce hydroxypropynamides 9 in good yields. Silation of 5a with chlorotrimethylsilane produces N‐benzyl‐3‐trimethylsilyl‐2‐propynamide (13) in high yield. Reduction of 9 furnishes either fully saturated amides 15 or partially reduced cis‐olefins 16 or 18. Compounds 16, on heating, rearrange to 4‐ketoamides 17. Carboxylation of 5a with carbon dioxide produces 3‐benzyl‐2,4‐dioxo‐5‐oxazidinylacetic acid (11). Warming 11 in dimethyl sulfoxide results in the loss of carbon dioxide and the formation of N‐benzylpyruvamide (21).
Regioselectivity of the metalation of polymethoxylated pivaloyl‐aminobenzenes. Synthesis of methoxy‐2(1H)‐quinolones precursors of 2‐substituted‐5,8‐quinolinediones
Authors: Fourquez J. M. , Godard A. , Marsais F. , Quéguiner G. 
Published: March 2009

AbstractSynthesis of methoxy‐2(1H)‐quinolones precursors of 2‐substituted‐5,8‐quinolinediones is described. A metalation, Heck coupling reaction and cyclisation sequence is used. Regioselectivity of the metalation of methoxypivaloylaminobenzenes is studied.
Reaction of 4,5‐diamino‐1,6‐dihydropyrimidin‐6‐ones with two equivalents of chalcones
Authors: Insuasty Braulio , Ramos Monica , Moreno Rodolfo , Quiroga Jairo , Sánchez Adolfo , Nogueras Manuel , Hanold Norbert , Meier Herbert 
Published: March 2009

AbstractThe reaction of 4,5‐diamino‐1,6‐dihydropyrimidin‐6‐ones 1 with two equivalents of the chalcones 2 leads in an acidic medium to the formation of the 2,3,6,7‐tetrahydro‐1H‐pyrimido[4,5‐b][1,4]diazepin‐6‐one derivatives 3a‐d. The structure elucidation of the products is based on nmr measurements and an X‐ray diffraction.
Reaction of 2,2′‐bis(N‐methylindolyl) with dimethyl acetylenedicarboxylate and thermally‐ and photochemically‐induced cyclizations of the product
Authors: Pindur U. , Kim Y. S. , Schollmeyer D. 
Published: March 2009

Abstract2,2′‐Bis(N‐methylindolyl) 1 reacts with dimethyl acetylenedicarboxylate to furnish the 3‐dimethyl maleoyl‐substituted 2,2′‐bisindolyl 2. Compound 2 cyclizes under aluminum trichloride catalysis according to a polar process to give a cyclopenta[2,1‐b:3,4‐b′]diindole derivative 4. Reaction of compound 4 with benzyl‐amine yields the spiro derivative 5. Photochemically‐induced 1,6‐electrocyclization of compound 2 gives rise to the indolo[2,3‐a]carbazole 6 directly, which is readily transformed to the pyrrolo‐annelated carbazole 7 by treatment with benzylamine.
Reactions of carbethoxycarbene with enaminones. Formation of unexpected pyrroles
Authors: Augusti Rodinei , Eberlin Marcos N. , Kascheres Concetta 
Published: March 2009

AbstractThe reactions of carbethoxycarbene (:CH2‐CO2Et, 2) with several acyclic enaminones (RCOCH=CR1NHR2, 3) lead to the unexpected formation of 2‐Me, 3‐CO2Et, 4‐H, 5‐R1‐pyrroles 4. Structural variations of the enaminones show that the structural fragments C(3)‐CO2Et and C(2)‐Me are provided by 2 and that the fragment C(5)‐R1NHR2 originates from the enaminones 3, while the RCO group from 3 is eliminated during the course of reaction. Reactions with cyclic and nitrogen‐hindered enaminones do not lead to pyrrole formation but occur by simple insertion of 2 to the Cα‐H bond.
4‐Alkoxycarbonyl, 4‐alkylthiocarbonyl and 5‐alkoxycarbonyloxy derivatives of 1‐substituted‐3‐methylpyrazol‐5‐ones
Authors: López Rodolfo , León Gerardo , Oliva Alfonso 
Published: March 2009

AbstractThe reaction of 1‐substituted‐3‐methylpyrazol‐5‐ones 1 with alkyl chloroformates and calcium hydroxide in dioxane have been studied. With 1‐phenyl‐3‐methylpyrazol‐5‐one, the isolated product was alkyl 3‐methyl‐5‐oxo‐1‐phenylpyrazole‐4‐carboxylate 2 but with 1‐alkyl‐3‐methylpyrazol‐5‐one formation of 1‐alkyl‐5‐alkoxycarbonyloxy‐3‐methylpyrazole 3 was observed. Replacement of alkyl chloroformate by bis(alkoxythiocarbonyl) sulfide results in the formation of 4‐alkoxythiocarbonyl derivatives 4 in low yield with both 1‐substituted‐3‐methylpyrazol‐5‐ones.
Nucleophilic aromatic substitution with the anion of 3,5‐disubstituted isoxazole‐4‐carboxylic acids
Authors: Mosher Michael D. , Natale Nicholas R. 
Published: March 2009

AbstractThe preparation of the anion of a series of protected 3,5‐disubstituted 4‐isoxazolecarboxylic acids and the resulting addition of the anion to 9‐chloroacridine is described. The addition‐elimination reaction proceeds to give the expected acridinylmethylisoxazoles and has been justified based on calculated molecular mechanics energies and solvent effects.
A convenient synthesis of diaminoglyoxime and diaminofurazan: Useful precursors for the synthesis of high density energetic materials
Authors: Gunasekaran Ananthakrishnan , Jayachandran Thiruvalam , Boyer Joseph H. , Trudell Mark L. 
Published: March 2009

AbstractThe reaction of glyoxime (4) and hydroxylamine hydrochloride in aqueous sodium hydroxide was found to be a safe and inexpensive method for the preparation of multigram quantities of diaminoglyoxime (5). Potassium hydroxide mediated dehydration of 5 furnished diaminofurazan (1) in good yield of exceptional purity. The ready availability of 1 and 5 has facilitated the synthesis of new energetic furazan derivative 8.
Synthesis of new oxazolidine, oxazolidin‐2‐one and perhydro‐1,4‐oxazine derivatives of arylethanolamine as potential beta3‐adrenoceptor agonists
Authors: Monge Antonio , Aldana Ignacio , Cerecetto Hugo , Rivero Argimiro 
Published: March 2009

AbstractThe synthesis of new cyclic compounds, arylethanolamine derivatives, with potential beta3‐adrenoceptor agonist selectivity, which are associated with thermogenesis and regulation of insulin release, are described. Oxazolidine, oxazolidin‐2‐one, and perhydro‐1,4‐oxazine derivatives were obtained. The preliminary evaluation of the pharmacological effects of some of the synthesized compounds showed an activation of lypolysis in rat adipocytes with potency and efficiency similar to that observed for other accredited beta3‐adrenergic agonists.
Intramolecular sulfoxide electrophilic sulfenylation in 1‐ and 3‐acylindoles
Authors: Bates Dallas K. , Habib Qazi A. 
Published: March 2009

AbstractHeating 1‐(2‐ethylsulfinyl)benzoylindole (1) in refluxing p‐xylene [thermal Sulfoxide Electrophilic Sulfenylation (SES)] produces indolo[2,1‐b][1,3]benzothiazin‐12‐one (2) in 66% yield. Similar treatment of 1‐methyl‐3‐(2‐ethylsulfinyl)benzoylindole (8) provides three products: sulfide 7 and cyclized products 9 and 10 in 10, 19 and 15% yield, respectively. Conversion of 10 to 9 under the reaction conditions is demonstrated and a spirocyclic intermediate 12, which may form from both 9 and 10 but undergoes only preferential S‐migration, is postulated to account for the rearrangement.
Synthesis and characterization of a novel octaphenyl substituted solvent soluble phthalocyanine
Authors: Yang Jiang , Van De Mark Michael R. 
Published: March 2009

AbstractNovel metal free, zine 1,2,3,4,15,16,17,18‐octaphenyl‐9,10,23,24‐tetradodecyloxyphthalocyanines were synthesized by condensation of excess 1,3‐diimino‐4,5,6,7‐tetraphenylisoindoline with 1,3‐diimino‐5,6‐bis(dodecyloxy)isoindoline. The compound was separated by gel permeation chromatography. The structure was confirmed by elemental analysis, 1H nmr, 13C nmr, uv‐vis and ir spectroscopy.
Conformational analysis of c3′‐c8 connected biflavones
Authors: Konda Yaeko , Sasaki Tomomitsu , Kagawa Hitoshi , Takayanagi Hiroaki , Harigaya Yoshihiro , Sun Xue‐Long , Li Xian , Onda Masayuki 
Published: March 2009

AbstractTwo biflavones isolated from Taxus cuspidata were identified with ginkgetin (1) and sciadopitysin (2) which belong to C3′‐C8 connected biflavones. The conformation of 2 in the solid state was determined by X‐ray analysis and the conformations of 1 and 2 in the liquid state were discussed using nmr techniques. Complete assignments of 1H and 13C nmr spectra about 1 were made on the basis of COSY, HMQC, HMBC and nOe experiments.
Tetrazole compounds. 10. Novel tetrazolylindoles by fischer indolization of substituted tetrazolylacetaldehyde phenylhydrazones
Authors: Fischer Gerhard W. 
Published: March 2009

AbstractThe acid‐catalyzed reaction of substituted phenylhydrazines 1 with 1‐aryl‐5‐(2‐dimethylaminovinyl)‐1H‐tetrazoles 2 afforded (1‐aryl‐1H‐tetrazol‐5‐yl)acetaldehyde phenylhydrazones 3 which on heating in acetic acid/perchloric acid underwent a Fischer indolization to give substituted 3‐(1‐aryl‐1H‐tetrazol‐5‐yl)‐indoles 4a‐k. Indoles of this type are also formed on subjecting 1 and 2 directly to indolization conditions; thus, starting from phenylhydrazine the tetrazolylindoles 41‐s were obtained by a one‐pot procedure. Indolization of corresponding Nα‐methylphenylhydrazones 5 resulted in 1‐methyl‐3‐(1‐aryl‐1H‐tetrazol‐5‐yl)indoles 6.
Synthesis of new thiazolium betaines and the ring expansion reaction via 1,4‐dipolar cycloaddition
Authors: Kim Dong Chan , Kim Dong Jin , Park Sang Woo , Ho Yoo Kyung 
Published: March 2009

AbstractThe 1,4‐dipolar cycloaddition of 3‐phenyl‐7‐[N‐pheny(carbamoyl)]‐5,6‐dihydroimidazo[2,1‐b]thia‐zolium betaine (7d) with a series of aliphatic alkylating agents such as ethyl bromoacetate, α‐chloroacetone, and ethyl 4‐chloroacetoacetate gave a variety of new ring‐expanded cycloadducts 10a‐c instead of ring transformation compounds 9. This result was derived from the difference of reactivity between N‐ and S‐alkylations of thiazolium betaines 7a,d. The advantage of our method is to prepare the triheterocyclic compounds 10a‐c of complicated structure using reactive thiazolium betaine 7d in a one‐pot without isolation of intermediates. Treatment of N‐bridged thiazolo compounds 1a‐c with benzoyl isothiocyanate led to new thiazolium betaines 2a‐c, which were reacted with methyl iodide to afford the S‐alkylated quarternary ammonium salts 3a‐c. Synthesis of new 2‐iminothiazolinium betaines 5a,b also was carried out.
Synthesis of α‐2′‐deoxynucleosides
Authors: Larsen Erik , Abdel Aleem Abdel Aleem H. , Pedersen Erik B. 
Published: March 2009

Abstractα‐Thymidine (4) was synthesized from thymidine (1) in 3 steps in 36% overall yield without using chro‐matography and with the possibility of increasing the yield to 85% by reusing the remaining α,β‐mixture. 1‐(2‐Deoxy‐3,5‐di‐O‐p‐toluoyl‐α‐D‐erythro‐pentofuranosyl)thymine (3) was further converted to 1‐(2‐deoxy‐α‐D‐erythro‐pentofuranosyl)‐5‐methylcytosine (5).
An approach to substituted 4‐hydroxypyran‐2‐ones
Authors: Ramirez Mai‐Ly , Garey Donna , Peña Michael R. 
Published: March 2009

AbstractWe examined a method for the preparation of 4‐hydroxypyran‐2‐ones in two steps from aryl ketones and ethyl malonyl chloride (or ethyl 2‐methylmalonyl chloride). These 4‐hydroxypyran‐2‐ones are useful precursors as they may be transformed in two steps to the 2‐methoxypyran‐4‐ones, which is found in phenoxan—a naturally occurring compound discovered to have anti‐HIV activity.
A convenient synthesis of a permethyl‐substituted β‐cyclodextrin‐containing polysiloxane stationary phase using an amide linking group
Authors: Yi Guoliang , Li Wenbao , Bradshaw Jerald S. , Malik Abdul , Lee Milton L. 
Published: March 2009

AbstractA novel amide‐linked permethyl‐substituted β‐cyclodextrin‐bound polysiloxane stationary phase was prepared in only four steps. First, mono(6‐O‐toluenesulfonyl)‐β‐cyclodextrin was treated with sodium azide. Second, the resulting azide derivative was treated with methyl iodide and base followed by reduction with hydrogen to give amine‐substituted permethylcyclodextrin 3. Third, cyclodextrin 3 was treated with p‐(allyloxy)benzoyl chloride to form 6A‐(p‐allyloxybenzamido)‐substituted permethyl‐β‐cyclodextrin 4. Lastly, β‐cyclodextrin 4 was hydrosilylated onto a polysiloxane backbone containing hydrogen, methyl, and p‐tolyl substituents. This new phase separated the enantiomers of certain chiral lactones and alcohols in capillary supercritical fluid chromatography.
Synthesis of pyrido[2,1‐b]‐ and thiazolo[2,3‐b]purines
Authors: Giudice Maria Rosaria Del , Borioni Anna , Mustazza Carlo , Gatta Franco 
Published: March 2009

AbstractSome pyrido[2,1‐b]‐ and thiazolo[2,3‐b]purines, tricyclic compounds structurally related to [1,2,4]triazolo[1,5‐c]quinazolines 1 have been synthesized with a view to study their possible adenosine and benzodiazepine receptors affinity.
Synthesis of a new pyrrolo[1,3]diazepine: 4H‐pyrrolo[1,2‐a]thieno[2,3‐e][1,3]diazepine
Authors: Daïch Abdelali , Ohier Philippe , Decroix Bernard 
Published: March 2009

AbstractThe 4H‐pyrrolo[1,2‐a]thieno[2,3‐e][1,3]diazepine (20) was synthesized by the one‐pot intramolecular cyclization of the appropriate nitroaldehyde 13. This key intermediate 13 was obtained by two pathways from methyl 3‐bromomethylthiophene‐2‐carboxylate (6).
The synthesis of novel polycyclic heterocyclic ring systems.. Benzo[e][1]benzothieno[3,2‐g][1]benzothiophenes
Authors: Sasaki Kenji , Tokuda Osamu , Hirota Takashi , Luo Jiann‐Kuan , Casüe Raymond N. 
Published: March 2009

AbstractThe novel polycyclic heterocyclic ring system compound, methyl 3‐chlorobenzo[e][1]benzothieno‐[3,2‐g][1]benzothiophene‐2‐carboxylate was synthesized. The assignment of its 1H and 13C nmr spectra was also accomplished by utilizing two‐dimensional nmr methods.
Reactions of 2,2′,5′,2′‐terfuran
Authors: Mcfarland J. W. , Howe B. M. , Lehmkuhler J. D. , Myers D. C. 
Published: March 2009

AbstractFormylation of 2,2′,5′,2′‐terfuran (1) with N‐methylformanilide and phosphorus oxychloride gave 5‐formyl‐2,2′,5′,2′‐terfuran (2) and 5,5′‐diformyl‐2,2′5′,2′‐terfuran (3). Reduction of 2 and 3 afforded 5‐hydroxymethyl‐2,2′,5′,2′‐terfuran (4) and 5,5′ dihydroxymethyl‐2,2′,5′,2′‐terfuran (5), respectively. Terfuran 1 reacted with phenylmagnesium bromide to give 5‐(phenylhydroxymethyl)‐2,2′,5′,2′‐terfuran (6), and was carbonated to 5‐carboxy 2,2′,5′,2′‐terfuran (7) and 5,5′‐dicarboxy‐2,2′,5′,2′‐terfuran (8). Bromination of 1 with N‐bromosuccinimide gave 5,5′‐dibromo 2,2′,5′,2′‐terfuran (9).
Synthesis and 1H, 19F NMR spectroscopic characterization of (pentafluorophenyl)3‐n (pyrazol‐1‐yl‐tetrafluorophenyl)n=1,2 porphyrins
Authors: Jagerovic Nadine , Fruchier Alain , Elguero JosÉ 
Published: March 2009

AbstractThree new porphyrins bearing in the meso positions 4‐(pyrazol‐1‐yl)‐2,3,5,6‐tetrafluorophenyl substituents have been prepared and characterized by nmr spectroscopy.
A convenient synthesis of functionalized 8‐ and 9‐aza‐1‐oxaspiro[5.5]undecanes
Authors: Apostolopoulos Costas D. , Haroutounian Serkos A. 
Published: March 2009

Abstract2‐Hydroxy‐8‐(or 9‐)aza‐1‐oxaspiro[5.5]undec‐3‐en‐5‐ones derived from their corresponding 2‐furfuryl alcohols were used as key intermediates for the convenient synthesis of several novel 8‐ and 9‐aza‐1‐oxaspiro[5.5]undecane derivatives.
Photocyclization reactions. Part 3. Synthesis of naphtho[1,8‐bc]‐furans and Cyclohepta[cd]benzofurans using photocyclization of 8‐alkoxy‐1,2,3,4‐tetrahydro‐1‐naphthalenones and 4‐alkoxy‐6,7,8,9‐tetrahydro‐5H‐benzocyclohepten‐5‐ones
Authors: Sharshira Essam Mohamed , Iwanami Haruki , Okamura Mutsuo , Hasegawa Eietsu , Horaguchi Takaaki 
Published: March 2009

AbstractPhotocyclization reactions were carried out on 8‐alkoxy‐1,2,3,4‐tetrahydro‐1‐naphthalenones (six‐membered ring ketones) 4a‐g and 4‐alkoxy‐6,7,8,9‐tetrahydro‐5H‐benzocyclohepten‐5‐ones (seven‐membered ring ketones) 5a‐e in acetonitrile. Irradiation of 4a‐f gave rearranged naphthyl alcohols 8a‐f as major products. In the case of 4g, 2a,3,4,5‐tetrahydronaphtho[1,8‐bc]furan‐2a‐ol 6g was obtained. In contrast, irradiation of 5a‐e afforded 2,2a,3,4,5,6‐hexahydrocyclohepta[cd]benzofuran‐2a‐ols 9a‐e in good yields. The difference in reactivities between 4a‐g and 5a‐e is attributed to the conformation of six‐ and seven‐membered rings. Conformational and substituent effects in cyclization step of 1,5‐biradicals are discussed along with reaction pathways.
Synthesis and theoretical calculations of novel 5‐aryl substituted 2,4,7‐trioxo and 4,7‐dioxo‐2‐thioxopyrido[2,3‐d]pyrimidines
Authors: Rodríguez René , Suárez Margarita , Ochoa Estael , Morales Alhmed , González Leandro , Martín Nazario , Quinteiro Margarita , Seoane Carlos , Soto José L. 
Published: March 2009

AbstractNew substituted pyrido[2,3‐d]pyrimidines 5 and 6 have been prepared in one‐step from the readily available 6‐amino‐2,4‐dioxotetrahydropyrimidine (1) or 6‐amino‐4‐oxo‐2‐thioxotetrahydropyrimidine (2) and the arylidene substituted Meldrum's acid. The substitution pattern of the ethylene moiety in compounds 5 and 6 results in a strong push‐pull electronic effect. The semiempirical calculations using the AM1 method reveal two equally favoured conformations showing a distorted geometry. The calculated charge density values confirm the observed 13C nmr chemical shifts.
Ketalizations of aryl ω‐(2‐imidazolyl)alkyl ketones by glycerol and 3‐mercapto‐1,2‐propanediol. synthesis and characterization of cis‐ and trans‐{2‐aryl‐2‐[ω‐(2‐imidazolyl)alkyl](1,3‐dioxolan‐4‐yl and 1,3‐oxathiolan‐5‐yl)}methanols
Authors: Kim Jang‐Woo , Davis Frank S. , Huang Liang‐Fu , Abdelaal Salma M. , Upadhyaya Subhash P. , Lee Jae Jeong , Bauer Ludwig 
Published: March 2009

AbstractAryl 2‐[(2‐imidazolyl)ethyl or 3‐(2‐imidazolyl)propyl]ketones were ketalized by glycerol or 3‐mercapto‐1,2‐propanediol in boiling benzene in the presence of 4‐toluenesulfonic acid to provide the title compounds. The aryl substituents are 4‐chloro‐, 4‐bromo‐, 4‐fluoro‐, or 2,4‐dichlorophenyl. While aryl (2‐imidazolyl)methyl ketones condensed with glycerol to form cis‐ and trans‐{2‐aryl‐2‐[(2‐imidazolyl)methyl]‐4‐(hydroxymethyl)}‐1,3‐dioxolanes, related condensations with 3‐mercapto‐1,2‐propanediol, under similar, or even more stringent reaction conditions, produced no 1,3‐oxathiolane analogs, with the starting ketones being recovered. Separation and structure determination of these racemic cis and trans isomeric products are described. The structure of these stereoisomers was established by means of 1H and 13C nmr correlation and nOe experiments. Selective methylation of the N‐unsubstituted 2‐imidazolyl alcohols with one equivalent sodium hydride and methyl iodide provided the corresponding N‐methyl alcohols in excellent yields. With excess benzoyl chloride, N‐unsubstituted 2‐imidazolyl alcohols were initially converted to O, N‐dibenzoates from which the N‐benzoyl group was easily cleaved by ammonium hydroxide in ethanol to provide benzoate esters.
Nitrogen configuration determined by X‐ray analysis on an homogeneous series of 3‐Indolinones
Authors: Carloni Patricia , Greci Lucedio , Stipa Pierluigi , Cauzzi Daniele , Rizzoli Corrado , Sgarabotto Paolo 
Published: March 2009

AbstractThe X‐ray diffraction analyses of 2‐methyl‐2‐phenylindolin‐3‐one 1, 1,2‐dimethyl‐2‐phenylindolin‐3‐one 2, 1‐hydroxy‐2‐methyl‐2‐phenylindolin‐3‐one 3 and 1‐methoxy‐2‐methyl‐2‐phenylindolin‐3‐one 4 have been carried out and the structural data were compared with those of 1‐oxyl‐2‐methyl‐2‐phenylindolin‐3‐one 5. The results demonstrate that only compounds 2 and 5 show planar trigonal geometry which is coplanar with the conjugated benzene ring of the indolinic nucleus, whereas compounds 3 and 4 show a marked pyramidality of the nitrogen. Even if compound 1 shows a certain pyramidality of the nitrogen, it has been considered similar to compound 2. The reactivity of all studied compounds fit the structural data.
Ring‐opening reactions of 3‐substituted 1‐azabicyclo[1.1.0]butane with dichlorocarbene
Authors: Mlostoń Grzegorz , Galindo Alberto , Bartnik Romuald , Marchand Alan R. , Rajagopal D. 
Published: March 2009

AbstractReaction of 3‐ethyl‐1‐azabicyclo[1.1.0]butane (1a) with chloroform‐potassium tert‐butoxide afforded a ring‐opened product, 1,1‐dichloro‐2‐aza‐4‐ethylpenta‐1,4‐diene (4a), which was characterized via conversion to the corresponding N‐substituted 5‐chloro‐1,2,3,4‐tetrazole, Sa. Reaction of 3‐phenyl‐1‐azabicyclo‐[1.1.0]butane (1b) with “Seyferth's reagent” (PhHgCCl2Br) afforded 1,1‐dichloro‐2‐aza‐4‐phenylpenta‐1,4‐diene (4b), which also was characterized via conversion to a tetrazole derivative, i.e., 5b. Finally, the reaction of 1b with dichlorocarbene generated under phase transfer conditions (chloroform‐sodium hydroxide‐TEBA) was studied. At short reaction times (0.5 hour), the major reaction product was 4b. However, at longer reaction times (20–30 hours), two secondary products, 8 and 9, were formed which resulted via subsequent dichlorocyclopropanation of 4b.
The synthesis of 3,4‐dihydro‐2‐methyl‐3‐oxo‐2H‐benzo‐1,4‐thiazine‐2‐carboxylic acids
Authors: Leskovšek Cizej V. , Urleb U. 
Published: March 2009

AbstractThe synthesis of 3,4‐dihydro‐2‐methyl‐3‐oxo‐2H‐benzo‐1,4‐thiazine‐2‐carboxylic acids 4a, b, 6a‐e is presented. After the condensation of o‐aminothiophenols with diethyl 2‐bromo‐2‐methylmalonate in the presence of KF as a catalyst the nitrogen in the fused derivatives 3a, b, was alkylated to provide 5a‐f, the corresponding esters 3a, b, 5a‐f were hydrolysed.
Photocyclization reactions. Part 4 . Synthesis of naphtho[1,8‐bc]‐furans and cyclohepta[cd]benzofurans using photocyclization of Ethyl 2‐(8‐Oxo‐5,6,7,8‐tetrahydro‐1‐naphthyloxy)acetates and ethyl 2‐(5‐Oxo‐6,7,8,9‐tetrahydro‐5H‐benzocyclohepten‐4‐yloxy)acetates
Authors: Sharshira Essam Mohamed , Iwanami Haruki , Okamura Mutsuo , Hasegawa Eietsu , Horaguchi Takaaki 
Published: March 2009

AbstractPhotocyclization reactions were carried out on ethyl 2‐(8‐oxo‐5,6,7,8‐tetrahydro‐1‐naphthyloxy)acetates 1a‐e and ethyl 2‐(5‐oxo‐6,7,8,9‐tetrahydro‐5H‐benzocyclohepten‐4‐yloxy)acetates 2a‐e in acetonitrile. Irradiation of 1a‐e gave naphtho[1,8‐bc]furanols 3a‐e and naphtho[1,8‐bc]furans 4a‐e in 33–83% yields and ethyl acrylates 5b‐d were produced in 3–25% yields during irradiation of 1b‐d. On the other hand, 2a‐e afforded cyclohepta[ad|benzofuranols 6a‐e and cyclohepta[ad]benzofurans 7a‐e in 44–87% yields. Ethyl acrylates 8b‐d were also produced in 7–43% yields from irradiation of 2b‐d. Substituent effects on photocyclization and reaction pathways are discussed.
Oligomers with four 3,4‐quinolinediyl units and α,ω‐bis (4‐chloro‐3‐quinolinylthio)alkanes
Authors: Boryczka Stanislaw , Rudnik Magdalena , Maślankiewicz Andrzej 
Published: March 2009

AbstractStarting from the reaction of thioquinanthrene 1 with sodium methoxide followed by the reaction with α,ω‐dihalogenoalkanes, title bis‐methoxy oligomers 4a‐c with four 3,4‐quinolinediyl units were prepared (40–91%). Acid catalysed hydrolysis of methoxy groups in 4a‐c gave tetramers 5a‐c (46–94%) with two 4(1H)‐quinolinone functions. The reactions of bis‐quinolinones 5a‐c with phosphoryl chloride in DMF run as deoxo‐chlorination and afforded tide dichlorotetramers 6a‐c (51–66%) with 4‐chloroquinolinyl groups. The treatment of bis‐methoxy tetramers 4a‐c with boiling phosphoryl chloride led to title α,ω‐bis(4‐chloro‐3‐quinolinylthio)alkanes 7a‐c (52–56%) and thioquinanthrene (65–70%).