- Push-pull-substituted oligo(2,5-thienyleneethynylene)s
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Oligo(2,5-thienyleneethynylene)s (OTE) with terminal donor-acceptor substitution were synthesized by applying Sonogashira-Hagihara reactions and a protection group technique. The combination of the alkylthio and nitro substituents provides a DAOTE series, whose long-wavelength absorption shows a monotonous bathochromic effect for increasing numbers n of repeat units. The convergence limit is already reached for n = 3. Georg Thieme Verlag Stuttgart.
- Muehling, Bastian,Theisinger, Sonja,Meier, Herbert
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- A successful chemical strategy to induce oligothiophene self-assembly into fibers with tunable shape and function
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Functional supramolecular architectures for bottom-up organic nano- and microtechnology are a high priority research topic. We discovered a new recognition algorithm, resulting from the combination of thioalkyl substituents and head-to-head regiochemistry of substitution, to induce the spontaneous self-assembly of sulfur overrich octathiophenes into supramolecular crystalline fibers combining high charge mobility and intense fluorescence. The fibers were grown on various types of surfaces either as superhelices or straight rods depending on molecular structure. Helical fibers directly grown on a field effect transistor displayed efficient charge mobility and intrinsic 'memory effect'. Despite the fact that the oligomers did not have chirality centers, one type of hand-helicity was always predominant in helical fibers, due to the interplay of molecular atropisomerism and supramolecular helicity induced by terminal substituents. Finally, we found that the new sulfur overrich oligothiophenes can easily be prepared in high yields through ultrasound and microwave assistance in green conditions.
- Di Maria, Francesca,Olivelli, Pasquale,Gazzano, Massimo,Zanelli, Alberto,Biasiucci, Mariano,Gigli, Giuseppe,Gentili, Denis,D'Angelo, Pasquale,Cavallini, Massimiliano,Barbarella, Giovanna
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supporting information; experimental part
p. 8654 - 8661
(2011/07/29)
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- Investigation of the aroma-active compounds formed in the maillard reaction between glutathione and reducing sugars
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Aroma-active compounds formed during the thermal reaction between glutathione (GSH) and reducing sugars were analyzed by gas chromatography-mass spectrometry (GC-MS) and GC-olfactometry (GC-O) with aroma extract dilution analysis (AEDA). Application of AEDA to glutathione Maillard reaction products (GSH MRPs) led to the identification of 19 aroma-active compounds in the thermal reaction of glutathione with glucose or fructose. In addition, the carbohydrate module labeling (CAMOLA) approach was also employed to elucidate the formation pathways for selected target sulfur aroma compounds, such as 5-methylthiophene-2-carbaldehyde and 3-methylthiophene-2-carbaldehyde, which have not been reported previously. The intact carbon skeleton of glucose via 3-deoxyhexosone is incorporated into 5-methylthiophene-2-carbaldehyde with the hydrogen sulfide of GSH. On the other hand, the formation of 3-methylthiophene2-carbaldehyde may occur via the recombination of a C-4 sugar fragment and mercaptoacetaldehyde.
- Lee, Sang Mi,Jo, Ye-Jin,Kim, Young-Suk
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experimental part
p. 3116 - 3124
(2011/08/05)
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- PROCESS FOR PREPARING DORZOLAMIDE HYDROCHLORIDE AND ITS INTERMEDIATE
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The present invention relates to an improved process for the preparation of (4S,6S)-4- (ethylamino)-5,6-dihydro-6-methyl-4H-thieno[2,3-b]thiopyran-2-sulfonamide-7,7-dioxide hydrochloride ("Dorzolamide hydrochloride") having formula 1. Dorzolamide hydrochloride is prepared by the process of the present invention with high chemical and diastereomeric purity. The present invention also relates to novel intermediate of the formula 20 and a process for its preparation. Dorzolamide hydrochloride is useful in the treatment of ocular hypertension by inhibiting carbonic anhydrase enzyme.
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Page/Page column 18-19; 24-25
(2010/06/17)
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- A simple, fast and chemoselective method for the preparation of arylthiols
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An efficient and convenient method for the synthesis of arylthiols by reaction of sulfonyl chlorides with triphenylphosphine in toluene is reported.
- Bellale, Eknath V.,Chaudhari, Mahesh K.,Akamanchi, Krishnacharya G.
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experimental part
p. 3211 - 3213
(2010/03/01)
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- Synthesis of sulphur compounds: Regioselective synthesis of thieno[2,3-b]thiophenes by sulfoxide rearrangement
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A number of thieno[2,3-b]thiophenes have been successfully synthesized in a 50-55% yield by m-chloroperoxybenzoic acid-mediated tandem cyclization involving [2, 3] and [3, 3] sigmatropic rearrangements and an intramolecular Michael addition. Copyright Taylor & Francis Group, LLC.
- Majumdar,Pal,Samanta
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p. 667 - 675
(2008/02/04)
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- Gas-phase reaction of 2-chlorothiophene with hydrogen sulfide in the presence of alcohols
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The effect of methanol and ethanol on the route of the gas-phase reaction of 2-chlorothiophene with hydrogen sulfide, leading to 2-thiophenethiol and to bis(2-thienyl) sulfide, has been investigated. It was found that methanol significantly enhances this
- Deryagina,Sukhomazova,Levanova
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- Polyhydroxyalkanoate and method of producing same, and omega-(2-thienylsulfanyl) alkanoic acid and method of producing same
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PHA containing a novel 3-hydroxy-thioalkanoic acid unit having a highly reactive thienyl group in a side chain thereof, and a method of producing the same are provided. Specifically, 5-(2-thienylsulfanyl) valeric acid represented by Chemical Formula [4] below and 6-(2-thienylsulfanyl) hexanoic acid represented by Chemical Formula [5] below are provided. Further, a method of producing PHA, comprising the step of collecting PHA from cells of a microorganism cultured in a medium containing the valeric acid or hexanoic acid, and a novel PHA represented by Chemical Formula [1] below are provided.(n denotes an integer of 1 to 9)
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- 4-Hydroxy-5,6-dihydro-2H-pyran-2-ones. 3. Bicyclic and hetero-aromatic ring systems as 3-position scaffolds to bind to S1' and S1' of the HIV-1 protease enzyme
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56-Dihydro-2H-pyran-2-ones are potent inhibitors of HIV-1 protease which bind to the S1 S2 S1' S2' pockets have a unique binding mode with the catalytic aspartyl groups the flap region of the enzyme. Efforts to explore 3-position heterocyclic scaffolds that bind to the S1' S2' pockets have provided a number of selected analogs that display high HIV-1 protease inhibitory activity.
- Ellsworth, Edmund L.,Domagala, John,Vara Prasad,Hagen, Susan,Ferguson, Donna,Holler, Tod,Hupe, Donald,Graham, Neil,Nouhan, Caroline,Tummino, Peter J.,Zeikus, Greg,Lunney, Elizabeth A.
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p. 2019 - 2024
(2007/10/03)
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- New structures able to prevent the inhibition by hydroxyl radicals of glutamate transport in cultured astrocytes
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4,5,6,7-Tetrahydro-benzothiophen-7-ylamines, 4,5,6,7-tetrahydro- benzothiophen-4-ylamines, and 5,6-dihydro-4H-thieno[2,3-b] thiopyran-4- ylamines were designed, synthesized, and tested as OH radical scavengers. Most of them displayed chemical scavenging properties better than or in the same range as salicylic acid. Moreover, some compounds were able to protect in vitro the astroglial glutamate transporters against inhibitory action of radicals promoted by xanthine/xanthine oxidase. Thus, such compounds might be useful for lowering the large amounts of excitotoxic glutamate liberated during acute CNS diseases: they might protect the glutamate reuptake in astrocytes from the inhibitory action due to radicals co-liberated with glutamate.
- Cauquil-Caubere, Isoline,Kamenka, Jean-Marc
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p. 867 - 877
(2007/10/03)
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- Organic compounds and their use as pharmaceuticals
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A pharmaceutically-active compound of the formula STR1 in which R1 is C1-4 alkythio, C1-4 alkylsulphinyl or C1-4 alkylsulphonyl, R2 is C1-4 alkyl, R3 is C1-4 alkyl or C2-4 alkenyl, and X is (i) --(CH2)n N(R4)2 where each R4 independently is C1-4 alkyl, C2-4 alkenyl or optionally substituted C6 H5 CH2 --, and n is 1, 2 or 3, or (ii) a 5- to 8-membered alicyclic group containing one or two nitrogen atoms and directly attached to the amido nitrogen or attached by a C1-3 alkylene chain; and salts thereof.
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- THERMAL TRANSFORMATIONS OF ALLYL 2-THIENYL SULFIDE AND SELENIDE
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In the gas phase at 350-410 deg C allyl 2-thienyl sulfide is converted to thiophene-2-thiol, di(2-thienyl) sulfide, and 2-methylthienothiophene.In the presence of acetylene thienothiophene is formed in addition to these products.Allyl 2-thienyl selenide is converted quantitatively to 2,3-dihydro-2-methylselenophenothiophene during fractional distillation in vacuo.Thiophene, di(2-thienyl) selenide, di(2-thienyl) diselenide, thiophene-2-selenol, and 2-methylselenophenothiophene are formed in addition to these compounds in the thermolysis ofallyl thienyl selenide in the gas phase.In the presence of acetylene the thermal decomposition of allyl thienyl selenide is accompanied by the formation of selenophene.
- Korchevin, N. A.,Sukhomazova, E. N.,Russavskaya, N. V.,Turchaninova, L. P.,Sigalov, M. V.,et al.
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p. 1049 - 1052
(2007/10/02)
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- FORMATION OF THIENOTHIOPHENES IN THE HIGH TEMPERATURE REACTION OF 2-CHLOROTHIOPHENE WITH COMPOUNDS CONTAINING THE C2H5S GROUP
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The high temperature gas-phase reaction of 2-chlorothiophene with a mixture of diethyl disulfide and diethyl trisulfide constitutes a simple one-step synthesis of a 4:1 mixture of thioeno- and thieno-thiophenes.Their total yield depends on the nature of the donor of the ethylthio group.
- Korchevin, N. A.,Sukhomoazova, E. N.,Turchaninova, L. P.,Efremova, G. G.,Kalinina, N. A.,et al
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p. 857 - 860
(2007/10/02)
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- NEW SYNTHESIS OF 1,2,5-SELENADIAZOLES
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A new synthesis of 1,2,5-selenadiazoles which starts from unsubstituted or monosubstituted 1,2,5-thiadiazoles and Grignard reagents is described and the mechanism of the reaction discussed.
- Bertini, Vincenzo,Munno, Angela De,Picci, Nevio,Lucchesini, Francesco,Pocci, Marco
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p. 2153 - 2158
(2007/10/02)
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- THERMAL HYDROTHIOLYSIS OF DI(2-THIENYL)SULFIDE IN THE GASEOUS AND LIQUID PHASE
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At 500-600 deg C, di(2-thienyl)sulfide is converted to thiophene, thiophene thiols, dithienyls, and dithienothiophenes, and isomerized to 2,3-dithienylsulfide.Hydrogen sulfide accelerates these reactions significantly.In the liquid phase the thermal conversion of di(2-thienyl)sulfide takes place only with the participation of elemental sulfur or in the system sulfur-hydrogen sulfide.Thiophene and diethienothiophenes are not formed in this case, while isomerization occurs to a large degree.The observed thermal conversions of di(2-thienyl)sulfide are based on the addition of thiyl radicals to the double bonds of the thiophene ring and to the sulfide sulfur atom.
- Voronkov, M. G.,Deryagina, E. N.,Papernaya, L. K.,Sukhomazova, E. N.,Korchevin, N. A.,Efremova, G. G.
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p. 1301 - 1306
(2007/10/02)
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- HIGH-TEMPERATURE ORGANIC SYNTHESIS. XXVII. REACTIONS OF ALKANETHIONES WITH THE CHLORINE DERIVATIVES OF BENZENE, THIOPHENE, AND NAPHTHALENE
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Alkanethiols react effectively with chlorobenzene, its derivatives, 1-chloronaphthalene, and 2-chlorothiophene at 600-660 deg C with the preferential formation of the corresponding aromatic or heteroatomic thiols.Ethanethiol is most reactive.When it is used instead of hydrogen sulfide in reactions with chlorobenzene or its 4-substituted derivatives, the yield of the aromatic thiols, from which the phenylthiyl radicals are generated with greater difficulty, increases more sharply than the yield of the thiophenols, which generate the more stable 4-XC6H4S radicals.The side products of the reactions are the corresponding diaryl sulfides, thiophene, benzothiophene, and toluene.
- Voronkov, M. G.,Deryagina, E. N.,Sukhomazova, E. N.
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p. 755 - 760
(2007/10/02)
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- RETENTION OF OPTICAL ACTIVITY IN THE THIO-CLAISEN REARRANGEMENT OF (-)-S-trans-(3-PENTEN-2-YL) 2-THIENYL SULFIDE
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The thio-Claisen rearrangement of (-)-S-trans-(3-penten-2-yl) 2-thienyl sulfide to the isomeric (+)-R-trans-3-(3-penten-2-yl)-2-thiophenethiol takes place with retention of the optical activity.This makes it possible to classify this reaction as concerted 3,3-sigmatropic shift.
- Anisimov, A.V.,Panov, S. M.,Egorov, A. M.,Viktorova, E. A.
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p. 367 - 369
(2007/10/02)
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- RADICAL IONS 49. Redox Reactions of some Thiphene Derivatives
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Trimethylsilyl- and cyano-substituted thiophenes can be reduced in THF using potassium and the resulting radical anions can be characterized by their electron spin resonance spectra.Attempts to oxidize thiophene derivatives with low first ionization potentials to their radical cations using the ALCl3/H2CCl2 oxidizing system failed except for dithienyldisulfide, the radical cation of which rearranges under the reaction conditions to the one of dithieno-p-dithiin.The photoelectron and electron spin resonance spectroscopic assignments are supported by MNDO as well as parametrized HMO calculations.
- Bock, H.,Roth, B.
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p. 211 - 224
(2007/10/02)
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- HIGH-TEMPERATURE ORGANIC SYNTHESIS. XVII. REACTION OF CHLOROBENZENE AND ITS DERIVATIVES WITH DIALKYL DISULFIDES
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The products from the reaction of chlorobenzene with dialkyl disulfides in the gas phase at 550-650 deg C are benzene, thiophenol, diphenyl sulfide, and also toluene, thiophene, and benzothiophene.Diethyl disulfide is most reactive.Its copyrolysis with chlorobenzene is distinguished by high selectivity for the formation of thiophenol, the yield of which amounts to 60percent.In the reaction of substituted chlorobenzenes and also 2-chlorothiophene and 1-chloronaphthalene with diethyl disulfide the corresponding thiols were obtained with high yields.Two paths for the formation of thiophene during the pyrolysis of dialkyl disulfide were established, i.e., from vinyl hydrosulfide and S-butyl radical.The last reaction is realized at a high rate.
- Voronkov, M. G.,Deryagina, E. N.,Sukhomazova, E. N.
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p. 1516 - 1522
(2007/10/02)
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- Aminopiperidines, their production and the pharmaceutical compositions incorporating them
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This invention relates to 4-aminopiperidines and more precisely to 4-aminopiperidines the nitrogen atom of the piperidine ring is substituted with an aryl lower alkyl side-chain. This invention also relates to processes for producing the same. This invention further extends to pharmaceutical compositions and to the method of using the same.
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- HIGH - TEMPERATURE ORGANIC SYNTHESIS. XIII. THE REACTIONS OF HYDROGEN SULFIDE WITH 1,2-DICHLOROETHYLENE
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1,2-Dichloroethylene reacts with hydrogen sulfide in the gas phase at 420 - 520 deg C in an empty quartz tube, forming bis(β-chlorovinyl)sulfide (geometric isomers), 2- and 3-chlorothiophene, 2,4-dichlorothiophene, 2- and 3-thienyl β-chlorovinyl sulfides (cis and trans isomers), cis-4-chloro-2-thienyl β-chlorovinyl sulfide, and thieno- and thienothiophenes.The yields of these compounds depend on the reaction conditions (temperature, contact time, ratio of initial reagents).At 480 deg C in an excess of 1,2-dichloroethylene the yield of the mixture of2- and 3-chlorothiophene amounts to 25percent (ratio 3 : 1).
- Perevalova, V. I.,Bannikova, O. B.,Deryagina, E. N.,Voronkov, M. G.
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p. 355 - 361
(2007/10/02)
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- A CONVENIENT SYNTHESIS OF AROMATIC THIOLS FROM UNACTIVATED ARYL HALIDES
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Aromatic thiols are obtained in good yields from unactivated aryl halides and excess MeSNa in HMPA.
- Testaferri, L.,Tingoli, M.,Tiecco, M.
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p. 3099 - 3100
(2007/10/02)
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