- A convenient preparation of thieno[3,2-c]pyrazole 1
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A practical synthesis of multigram quantities of 1H-thi-eno[3,2-c]pyrazole is presented in which the Jacobson reaction serves as the key step. Georg Thieme Verlag Stuttgart · New York.
- Airey, John,Barrague, Matthieu,Edwards, Michael L.,Ferro, Michael,Friedrich, Dirk,Gillespy, Timothy A.,Jurcak, John,Musick, Kwon,Weintraub, Philip M.
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Read Online
- INDACENO DERIVATIVES AS ORGANIC SEMICONDUCTORS
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The present invention provides compounds comprising at least one unit of formula (1) or (1') as well as a process for the preparation of the compounds, intermediates of this process, electronic devices comprising the compounds, and the use of the compounds as semiconducting materials.
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Page/Page column 59; 60
(2020/05/21)
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- The Effect of Ring Expansion in Thienobenzo[ b]indacenodithiophene Polymers for Organic Field-Effect Transistors
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A fused donor, thienobenzo[b]indacenodithiophene (TBIDT), was designed and synthesized using a novel acid-promoted cascade ring closure strategy, and then copolymerized with a benzothiadiazole (BT) monomer. The backbone of TBIDT is an expansion of the well-known indacenodithiophene (IDT) unit and was expected to enhance the charge carrier mobility by improving backbone planarity and facilitating short contacts between polymer chains. However, the optimized field-effect transistors demonstrated an average saturation hole mobility of 0.9 cm2 V-1 s-1, lower than the performance of IDT-BT (~1.5 cm2 V-1 s-1). Mobilities extracted from time-resolved microwave conductivity measurements were consistent with the trend in hole mobilities in organic field-effect transistor devices. Scanning tunneling microscopy measurements and computational modeling illustrated that TBIDT-BT exhibits a less ordered microstructure in comparison to IDT-BT. This reveals that a regular side-chain packing density, independent of conformational isomers, is critical to avoid local free volume due to irregular packing, which can host trapping impurities. DFT calculations indicated that TBIDT-BT, despite containing a larger, planar unit, showed less stabilization of planar backbone geometries in comparison to IDT-BT. This is due to the reduced electrostatic stabilizing interactions between the peripheral thiophene of the fused core and the BT unit, resulting in a reduction of the barrier to rotation around the single bond. These insights provide a greater understanding of the general structure-property relationships required for semiconducting polymer repeat units to ensure optimal backbone planarization, as illustrated with IDT-type units, guiding the design of novel semiconducting polymers with extended fused backbones for high-performance field-effect transistors.
- Chen, Hu,Wadsworth, Andrew,Ma, Chun,Nanni, Alice,Zhang, Weimin,Nikolka, Mark,Luci, Alexander M. T.,Perdig?o, Luís M. A.,Thorley, Karl J.,Cendra, Camila,Larson, Bryon,Rumbles, Garry,Anthopoulos, Thomas D.,Salleo, Alberto,Costantini, Giovanni,Sirringhaus, Henning,McCulloch, Iain
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supporting information
p. 18806 - 18813
(2019/11/28)
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- Small isomeric push-pull chromophores based on thienothiophenes with tunable optical (non)linearities
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Fourteen new D-π-A push-pull chromophores based on two isomeric thienothiophene donors and seven acceptors of various electronic natures have been designed and conveniently synthesized. In contrast to known thienothiophene push-pull molecules, the prepared small chromophores proved to be organic materials with easily tunable thermal, electrochemical and (non)linear optical properties. It has also been shown that small structural variation may result in significantly improved/varied fundamental properties. Very detailed structure-property relationships were elucidated within the systematically developed series of push-pull molecules, which may serve as a useful guide in designing new D-π-A molecules based on fused thiophene scaffolds.
- Podlesny, Jan,Pytela, Old?ich,Klikar, Milan,Jelínková, Veronika,Kityk, Iwan V.,Ozga, Katarzyna,Jedryka, Jaroslaw,Rudysh, Myron,Bure?, Filip
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p. 3623 - 3634
(2019/04/14)
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- Convergent Synthesis of Fluorene Derivatives by a Rhodium-Catalyzed Stitching Reaction/Alkene Isomerization Sequence
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A convergent synthetic method for the synthesis of fluorene derivatives has been developed by devising a rhodium-catalyzed stitching reaction/alkene isomerization sequence. The reactions proceed smoothly under mild conditions for a variety of substrate combinations, and extended π-conjugation systems are also readily accessible by utilizing this synthetic method. Optical properties of the obtained fluorene derivatives have also been examined.
- Nishida, Masaki,Shintani, Ryo
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supporting information
p. 7475 - 7479
(2019/05/16)
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- Synthesis of N-Substituted Condensed Tetrahydropyridine-Based Enaminones via Palladium-Catalyzed Intramolecular C–N Cross-coupling
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A number of β-enaminones with secondary amino group (alkyl, cyclopropyl, and aryl) were prepared from corresponding β-diketones. Two general protocols for their palladium-catalyzed intramolecular C–N cross-coupling were established to give corresponding N-substituted condensed tetrahydropyridines in good yields. The methodology is applicable for a wide variety of structural motifs. The work also extends the applicability of novel, recently established, palladium precatalysts to new substrates.
- Dou?ová, Hana,R??i?ková, Zdeňka,?im?nek, Petr
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supporting information
p. 670 - 684
(2018/01/22)
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- Organic semiconducting compounds, manufacturing method thereof, and organic electronics devices containing the same
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The present invention relates to an organic semiconductor compound of an organic thin film transistor comprising a thiophene vinylene monomer into which a cyano substituent is introduced at the position 3; a method for producing the same; and an organic electronic device containing the same. The organic semiconductor compound of the present invention has low LUMO energy level, and high thermal stability and solubility, and exhibits excellent n-type electron transfer characteristics in an organic electronic device including the same, particularly an organic thin film transistor device.COPYRIGHT KIPO 2018
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Paragraph 0102-0105
(2018/04/21)
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- Enhanced electrochromic performances of Polythieno[3,2-b]thiophene with multicolor conversion via embedding EDOT segment
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A heterocyclic oligomer, thieno[3,2-b]thiophene (TT) end-capped famous 3,4-ethylenedioxythiophene (EDOT) unit and their electrosynthesized polymer P(TT-EDOT-TT) have been facilely achieved. To in-depth understand the effects of structural modification on physico-chemical properties and electrochromic performances of monomers and/or polymers, the absorption spectroscopy, electrochemistry, micromorphology, and spectroelectrochemistry were systematically studied. In contrast to TT and EDOT, TT-EDOT-TT possessed extended π-conjugation and narrowed band gap in molecular level. Through carefully comparison with PTT, it has been found that the electrochromic performances of P(TT-EDOT-TT) film exhibited much higher optical contrast (69%, while 3% for PTT in the near-infrared region) and superior coloring efficiency (255.3 cm2 C?1, while 36.8 cm2 C?1 for PTT), and switching times (within 1 s, while more than 9 s for PTT). Notably, P(TT-EDOT-TT) film can achieve the mutual conversion between RGB primary colors (red–green–blue) under variable voltages, which hold quite promising for display applications.
- Xue, Yu,Xue, Zexu,Zhang, Wenwen,Zhang, Wenna,Chen, Shuai,Lin, Kaiwen,Xu, Jingkun
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p. 150 - 156
(2018/11/30)
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- A new alkyl substituted and method for the synthesis of polythiophene
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The invention provides a method for replacing multi-thiophthene with beta-dialkyl in a synthesis formula I. The method comprises the following steps of: (f) reacting an intermediate in a formula 10 to obtain an intermediate in a formula 11; (g) reacting the intermediate in the formula 11 to obtain an intermediate in a formula 12; (h) reacting the intermediate in the formula 12 to obtain an intermediate in a formula 13; (i) reacting the intermediate in the formula 13 to obtain an intermediate in a formula 8; (j) reacting the intermediate in the formula 8 to obtain an intermediate in a formula 9; and (k) reacting the intermediate in the formula 9 to obtain a compound in a formula I. The invention further relates to the intermediate in the formula 9. The method disclosed by the invention is low in cost, simple in process, high in yield and low in pollution. The formulas 10, 11, 12, 13, 8 and 9 are shown in the description.
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Paragraph 0101-0104
(2017/01/05)
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- Synthesis, Fluorescence, and Two-Photon Absorption Properties of Push–Pull 5-Arylthieno[3,2-b]thiophene Derivatives
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Three series of novel push–pull 5-arylthieno[3,2-b]thiophene derivatives functionalized with potent electron-withdrawing terminal moieties have been synthesized in moderate to excellent yields by Suzuki coupling followed by Knoevenagel condensation. These novel chromophores show intense absorption in the near-UV region through to the orange visible region, related to a strong intramolecular charge-transfer transition. By combining a strong donor and acceptor, large fluorescence quantum yields were achieved as well as large two-photon absorption responses. Interestingly, due to the improved rigidity and electronic delocalization provided by the thienothiophene moiety (as compared with the bithiophene unit), higher one- and two-photon brightness values have been achieved. As a result, several new fluorescent dyes showing enhanced brightness and tunable fluorescence (ranging from the blue to the NIR region) have been obtained that have potential for bioimaging applications.
- Manuela,Raposo,Herbivo, Cyril,Hugues, Vincent,Clermont, Guillaume,Castro, M. Cidália R.,Comel, Alain,Blanchard-Desce, Mireille
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p. 5263 - 5273
(2016/11/13)
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- Tandem Pd-catalyzed C-C coupling/recyclization of 2-(2-bromoaryl)cyclopropane-1,1-dicarboxylates with primary nitro alkanes
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The first successful synthesis of 1H-2,3-benzoxazine 3-oxides has been described. The efficiency of the approach is provided by the C-C-coupling of 2-(2-bromoaryl)cyclopropane-1,1-dicarboxylates with primary nitroalkanes catalyzed by Pd(dba)2/JohnPhos system followed by in situ recyclization of the intermediates. Several representative transformations allowing selective modification of the nitronate as well as malonate functionalities in the resulting compounds are demonstrated.
- Mikhaylov, Andrey A.,Dilman, Alexander D.,Novikov, Roman A.,Khoroshutina, Yulia A.,Struchkova, Marina I.,Arkhipov, Dmitry E.,Nelyubina, Yulia V.,Tabolin, Andrey A.,Ioffe, Sema L.
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supporting information
p. 11 - 14
(2015/12/23)
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- FUSED DIHYDRO-4H-PYRAZOLO[5,1-C][1,4]OXAZINYL COMPOUNDS AND ANALOGS FOR TREATING CNS DISORDERS
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Disclosed are compounds of Formula (I) and pharmaceutically acceptable salts thereof, wherein Ring B, A1, A2, R6, w and n1 are defined and described herein; compositions thereof; and methods of use thereof. These compounds are useful for treating a variety of neurological and psychiatric disorders, such as those described herein.
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Paragraph 0202
(2016/09/22)
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- Design, synthesis, and anticancer activity of novel aryl/heteroaryl chalcone derivatives
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A new series of chalcones 5a-l were synthesized and evaluated for in vitro antiproliferative activity against human colon cancer cell lines. The synthesis of the key intermediate compounds 3a-d was achieved by tetrakis(triphenylphosphine) palladium(II) mediated Suzuki cross coupling reaction. Chalcone 5a shows superior anticancer activity with IC50 value of 21.0 μg/mL compared to the IC50 value of the reference drug doxorubicin at 21.65 μg/mL.
- Arasavelli, Ananda Mohan,Raghava Sharma, Ganapavarapu Veera,Vidavalur, Siddaiah
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- Correlation of structure and photovoltaic performance of benzo[1,2-b:4,5-b′]dithiophene copolymers alternating with different acceptors
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Four π-conjugated benzo[1,2-b:4,5-b′]dithiophene (BDT) based polymers were synthesized for application in polymer solar cells. These polymers possessed desirable HOMO/LUMO levels for polymer photovoltaic applications. PBDTT-TTz and PBDTT-DTBT displayed strong absorption in the range of 300-650 nm, while PBDTT-DPP and PBDTT-TTDPP showed a further 100 nm extended absorption band. The lowest unoccupied molecular orbital energy levels of polymers were tuned effectively from -3.34 eV to -3.81 eV by fusing with different accepting units. A maximum power conversion efficiency of 2.60% was obtained from photovoltaic cells with a PBDTT-TTz:PC61BM (1:2, w/w) blend film as the active layer, with a short circuit current density of 8.37 mA cm-2, an open circuit voltage of 0.70 V, and a fill factor of 44.3%. This journal is
- Yu, Jiangsheng,Zhao, Baofeng,Nie, Xuemei,Zhou, Baojin,Li, Yang,Hai, Jiefeng,Zhu, Enwei,Bian, Linyi,Wu, Hongbin,Tang, Weihua
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supporting information
p. 2248 - 2255
(2015/03/18)
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- HETEROACENES FOR ORGANIC ELECTRONICS
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The present invention provides compounds of formula 1 wherein X1 and X2 are independently from each other O, S or Se, and an electronic device comprising the compounds as semiconducting material.
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Page/Page column 28
(2015/09/28)
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- ARYL RECEPTOR MODULATORS AND METHODS OF MAKING AND USING THE SAME
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The present invention is generally directed towards compounds capable of binding the aryl hydrocarbon receptor and modulating its activity,methods of treating inflammatory conditions such as Crohn's disease using such compounds, and pharmaceutical compositions comprising such compounds. Also provided are methods of increasing levels of IL-22 in a subject and/or decreasing levels of IFN-γ in a subject.
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Paragraph 00173-00174
(2016/04/26)
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- Conjugated polymer for organic thin-film transistor comprising of Quinoxaline and Thieno[3,2-b]thiophene
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The present invention refers to [...] thieno [3, 2-b] thiophene using organic thin film transistor (organic thin-film transistor, OTFT) (conjugated polymer) relates to conjugated macromolecule type transition for electrolyte, more particularly 2, 3-bis (4- [...]) [...] -5, 8-(2, -5, 8-dibromoquinoxaline 3-Bis (4-hexylphenyl)) and 2, 5-bis (tri-n-methyl [...])-thieno [3, 2-b] thiophene (2, 5-Bis (Tri-n-methylstannyl)-thieno [3, 2-b] thiophene) Stille-coupling reactions of a produced through forging by use of conjugated macromolecule relates to (conjugated polymer). The present invention according to a heat conjugated macromolecule , each -3.3eV and -5.1eV HOMO and a LUMO value, the (band gap energy) 1.8eV band gap energy to useful as for anti-organic solar cells can be used. (by machine translation)
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Paragraph 0021; 0022; 0023
(2016/12/12)
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- Thiophene-fused borepins as directly functionalizable boron-containing π-electron systems
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Synthetic protocols were developed for the gram-scale preparation of two isomeric dithienoborepins (DTBs), boron-containing polycyclic aromatics featuring the fusion of borepin and thiophene rings. DTBs exhibit reversible cathodic electrochemistry and boron-centered Lewis acidity in addition to enhanced electronic delocalization relative to benzo-fused analogues. Borons precise position within the conjugation pathway of DTBs significantly affected electronic structure, most clearly demonstrated by the variation in spectroscopic responses of each isomer to fluoride ion binding. In addition to excellent stability in the presence of air and moisture, DTBs could also be subjected to electrophilic aromatic substitution and metalation chemistry, the latter enabling the direct, regiospecific functionalization of the unsubstituted thiophene rings. Subsequent tuning of molecular properties was achieved through installation of donor and acceptor π-substituents, leading to compounds featuring multistep electrochemical reductions and polarizable electronic structures. As rare examples of directly functionalizable, π-conjugated, boron-containing polycyclic aromatics, DTBs are promising building blocks for the next generation of organoboron π-electron materials whose development will demand broad scope for molecular diversification in addition to chemical robustness.
- Levine, David R.,Siegler, Maxime A.,Tovar, John D.
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supporting information
p. 7132 - 7139
(2014/06/09)
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- Optical activity of heteroaromatic conjugated polymer films prepared by asymmetric electrochemical polymerization in cholesteric liquid crystals: Structural function for chiral induction
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We electrochemically polymerized various achiral heteroaromatic monomers in left-handed helical cholesteric liquid crystal (CLC) media. Circular dichroism (CD) spectroscopy revealed that most of the resulting conjugated polymer films exhibited both the first negative and second positive Cotton effects near their absorption maxima. This indicates left-handed helical aggregation of the conjugated main chains, which is consistent with left-handed helical order of the CLC. This result suggests that the left-handed helical CLC environment induced left-handed helical aggregation of the polymers during the electrodeposition. However, CD intensity of the polymers depends on the structure of the parent monomers. Systematic investigation of the relationship between monomer structures and optical activity of the polymers indicates that linearity of the conjugated main chains and excluded volume interaction between the monomers and the CLC are important factors for producing optical activity of the polymers.
- Kawabata, Kohsuke,Takeguchi, Masaki,Goto, Hiromasa
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p. 2078 - 2091
(2013/06/04)
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- Directed metalation and regioselective functionalization of 3-bromofuran and related heterocycles with NaHMDS
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A mild and regioselective functionalization protocol for 3-bromofuran and analogs has been developed. Selective metalation and functionalization of C2 can be achieved as a result of the directing effect of the adjacent electron-withdrawing bromo group. In addition, the C5 position can also be selectively functionalized by blocking the C2 position via silylation or by simply controlling the reaction temperature. These functionalized compounds bearing a C3 bromo substituent may be further elaborated by utilizing a Suzuki-Miyaura cross-coupling procedure.
- Zhao, Hang,Dankwardt, John W.,Koenig, Stefan G.,Singh, Surendra P.
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supporting information; experimental part
p. 166 - 169
(2012/01/30)
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- N-TYPE ORGANIC SEMICONDUCTORS INCLUDING AT LEAST TWO 2-DICYANOMETHYLENE-3-CYANO-2,5-DIHYDROFURAN GROUPS
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The invention relates to a method for manufacturing transistors. Said method involves using a molecule including at least two 2-dicyanomethylene-3-cyano-2,5-dihydrofuran groups. The invention can be implemented in particular in the field of electronics.
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Page/Page column 16
(2012/05/20)
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- Versatile α,ω-disubstituted tetrathienoacene semiconductors for high performance organic thin-film transistors
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Facile one-pot [1 + 1 + 2] and [2 + 1 + 1] syntheses of thieno[3,2-b]thieno[2′,3′:4,5]thieno[2,3-d]thiophene (tetrathienoacene; TTA) semiconductors are described which enable the efficient realization of a new TTA-based series for organic thin-film transistors (OTFTs). For the perfluorophenyl end-functionalized derivative DFP-TTA, the molecular structure is determined by single-crystal X-ray diffraction. This material exhibits n-channel transport with a mobility as high as 0.30 cm 2V-1s-1 and a high on-off ratio of 1.8 × 107. Thus, DFP-TTA has one of the highest electron mobilities of any fused thiophene semiconductor yet discovered. For the phenyl-substituted analogue, DP-TTA, p-channel transport is observed with a mobility as high as 0.21 cm2V-1s-1. For the 2-benzothiazolyl (BS-) containing derivative, DBS-TTA, p-channel transport is still exhibited with a hole mobility close to 2 × 10-3 cm2V -1s-1. Within this family, carrier mobility magnitudes are strongly dependent on the semiconductor growth conditions and the gate dielectric surface treatment. Copyright
- Youn, Jangdae,Huang, Peng-Yi,Huang, Yu-Wen,Chen, Ming-Chou,Lin, Yu-Jou,Huang, Hui,Ortiz, Rocio Ponce,Stern, Charlotte,Chung, Ming-Che,Feng, Chieh-Yuan,Chen, Liang-Hsiang,Facchetti, Antonio,Marks, Tobin J.
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scheme or table
p. 48 - 60
(2012/05/05)
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- Synthesis and characterization of new thieno[3,2-b]thiophene derivatives
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Three derivatives of thieno[3,2-b]thiophene end-capped with phenyl units have been synthesized and characterized by MALDI TOF mass spectroscopy, elemental analysis, UV-vis absorption spectroscopy and thermogravimetric analysis (TGA). All compounds were prepared using Pd-catalyzed Stille or Suzuki coupling reactions. Optical measurements and thermal analysis revealed that these compounds are promising candidates for p-type organic semiconductor applications.
- Ahmed, Moawia O.,Pisula, Wojciech,Mhaisalkar, Subodh G.
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p. 12163 - 12171
(2013/01/15)
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- Highly emissive and electrochemically stable thienylene vinylene oligomers and copolymers: An unusual effect of alkylsulfanyl substituents
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The synthesis, unexpected efficient photoluminescence, and reversible electrochemical p- and n-doping of new conjugated thienylene vinylene materials functionalized with alkylsulfanyl substituents poly(trithienylene vinylene) (PTTV) and poly(dithienylvinyl-co-benzothiadiazole) (PDTVB) along with dithienylvinylene-based oligomers is reported. The materials are studied by thermal and X-ray diffraction analysis, optical spectroscopy, cyclic voltammetry, and spectroelectrochemistry. Organic field-effect transistors (OFETs) are fabricated with PTTV and PDTVB. The polymers, prepared by Stille polycondensation, exhibit good thermal stability and a photoluminescent quantum yield in the range 34%-68%. Low bandgaps (1.5-1.8 eV), estimated by optical and electrochemical measurements along with high stability of both redox states, suggest that these structures are promising materials for photovoltaic applications. OFETs fabricated with PDTVB reveal a hole mobility of 7 × 10-3 cm2 V-1 s-1 with on/off ratio 105, which are comparatively high values for completely amorphous polymer semiconductors.
- Jeeva, Shehzad,Lukoyanova, Olena,Karas, Athan,Dadvand, Afshin,Rosei, Federico,Perepichka, Dmitrii F.
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experimental part
p. 1661 - 1669
(2011/12/02)
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- Selective metallation of 3-halothiophenes: Practical methods for the synthesis of 2-bromo-3-formylthiophene
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Selective lithiation of 3-bromothiophene was accomplished under controlled conditions without formation of undesired thienyllithium compounds. A thienyl Grignard reagent derived from 2-bromo-3-iodothiophene was transformed into 2-bromo-3-formylthiophene in high selectivity by formylation with dimethylformamide (DMF) at optimal reaction temperature. Copyright Taylor & Francis Group, LLC.
- Sonoda, Motohiro,Kinoshita, Shoko,Luu, Thanh,Fukuda, Hiroshi,Miki, Koji,Umeda, Rui,Tobe, Yoshito
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experimental part
p. 3315 - 3323
(2011/03/20)
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- Synthesis of 9-amino-5,6,7,8-tetrahydrothieno[3,2-b]quinoline and 9-amino-5,6,7,8-tetrahydrothieno[3,2-b]quinolin-8-ol derivatives
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(Chemical Equation Presented) The synthesis of 9-amino-5,6,7,8- tetrahydrothieno[3,2-b]quinoline (3) and 9-amino-5,6,7,8-tetrahydrothieno[ 3,2-b]quinolin-5-ol derivatives (4a-g) in good yield by three-step procedures starting from 3-aminothiophene-2-carbonitrile and 5-substituted cyclohexane-1,3-dione is described.
- Song, Yang-Heon,Jo, Boung Sun
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experimental part
p. 1132 - 1136
(2010/03/03)
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- Thiophene bioisosteres of spirocyclic σ receptor ligands. 1. N-substituted spiro[piperidine-4,4′-thieno[3,2-c]pyrans]
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Herein, the synthesis and pharmacological evaluation of thiophene bioisosteres of the highly potent spirocyclic benzopyran 1 are detailed. The synthesis of 1-benzyl-6′-methoxy-6′,7′- dihydrospiro[piperidine-4,4′-thieno[3.2-c]pyran] (2a) was performed starting with 3-bromothiophene (3). After introduction of the acetaldehyde substructure (7), halogen metal exchange, addition of 1-benzylpiperidin-4-one, and cyclization led to the spirocyclic thienopyran 2a. The removal of the benzyl group afforded the secondary amine 2f, which was substituted with various residues. With respect to σ1 affinity the N-benzyl derivative 2a, the N-cyclohexylmethyl derivative 2d, and the N-p-fluorobenzyl derivative 2i represent the most potent compounds of this series binding with Ki values of 0.32, 0.29, and 0.62 nM, respectively. Electronic properties of the substituents have only little impact on σ1 affinity. The most potent σ1 ligands display high selectivity against σ2, 5-HT1A, 5-HT6, 5-HT7, α1A, α2, and NMDA receptors. The activity of 2a in the mouse capsaicin assay seems to indicate σ1 antagonistic activity.
- Oberdorf, Christoph,Schepmann, Dirk,Vela, Jose Miguel,Diaz, Jose Luis,Holenz, J?rg,Wünsch, Bernhard
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supporting information; body text
p. 6531 - 6537
(2009/10/17)
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- SPIRO [PIPERIDINE-4, 4' -THIENO [3, 2-C] PYRAN] DERIVATIVES AND RELATED COMPOUNDS AS INHIBITORS OF THE SIGMA RECEPTOR FOR THE TREATMENT OF PSYCHOSIS
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The present invention relates to compounds having pharmacological activity towards the sigma (s) receptor, and more particularly to some thieno-pyrano-pyrazole derivatives, to processes of preparation of such compounds, to pharmaceutical compositions comprising them, and to their use in therapy and prophylaxis, in particular for the treatment of psychosis or pain.
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Page/Page column 40-41
(2009/01/23)
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- A versatile aminobenzannulation method based on the deprotonation of 2-(1-alkynyl)-benzaldimines and similar 2-aza-2,4-heptadienyl-6-ynes: A multistep rearrangement cascade
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Two ring closures, a ring opening, and two intermolecular proton shifts are the crucial steps in a cascade reaction that is triggered by the simple deprotonation of alkynylimines and leads ultimately to aminobenzannulation products (see scheme). The reactions proceed in good to very good yield and with excellent chemoselectivity.
- Sagar, Pramod,Froehlich, Roland,Wuerthwein, Ernst-Ulrich
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p. 5694 - 5697
(2007/10/03)
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- Fused pyridine derivatives
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The present provides a condensed pyridine compound (I) represented by the following formula: (wherein, R2represents ring A represents benzene ring, pyridine ring, thiophene ring or furan ring; and B represents its pharmaceutically acceptable salt or hydrates thereof, which is a clinically useful medicament having a serotonin antagonism, in particular, that for treating, ameliorating or preventing spastic paralysis or central muscle relaxants for ameliorating myotonia.
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- Synthesis of novel chiral thiophene-, benzothiophene- and benzofuran-oxazoline ligands and their use in the enantioselective Pd-catalyzed allylation
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Novel thiophene, benzothiophene and benzofuran-oxazoline ligands 6-11 containing a diphenylphosphino group at different positions of the heterocyclic skeleton have been prepared and used in the enantioselective allylation. The advantage of these new ligands is their easy accessibility and their high reactivity. The best results were obtained with ligand 9 to give the product 13 in 97.0% ee with 92% yield in 2 hours at 0°C.
- Tietze, Lutz F.,Lohmann, J. Klaas
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p. 2083 - 2085
(2007/10/03)
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- Cell adhesion-inhibiting antiinflammatory compounds
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Compounds having Formula I are useful for treating inflammation. Also disclosed are pharmaceutical compositions comprising compounds of Formula I, and methods of inhibiting/treating inflammatory diseases in a mammal.
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- Regioselective electrophilic formylation - 3-substituted thiophenes as a case study
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A variety of methods for regioselective formylation have been examined and exemplified with 3-methylthiophene. Optimal yields and regioselectivity for 2-formylation were obtained with N-formylpyrrolidine (11:1) although up to a 46:1 ratio could be obtained with MeOCHCl2:TiCl4, albeit in lower yield. Optimal 5-formylation (1:1.5) was obtained when using N- formylindoline:(COCl)2. (C) 2000 Elsevier Science Ltd.
- Meth-Cohn, Otto,Ashton, Mark
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p. 2749 - 2752
(2007/10/03)
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- Oxaboroles and salts thereof, and their use as biocides
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A method for the protection of a medium by susceptible to microbial attack by the treatment of the medium with an oxaborale or a salt of an oxaborale.
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- 4-(THIEN-2-YL)METHYL]-IMIDAZOLE ANALGESICS
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The 4-[(thien-2-yl)methyl]-imidazoles of the formulae: STR1 wherein R is hydrogen or methyl,X is hydrogen, C 1-4 alkyl, bromine or chlorine, andY is hydrogen, C 1-4 alkyl, bromine or chlorine;with the proviso that X and Y are not both simultaneously hydrogen.have exceptional analgesic activity.
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- Thienothiophenes. Part 2. Synthesis, metallation and bromine→lithium exchange reactions of thieno[3,2-b]thiophene and its polybromo derivatives
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Methods for the large-scale synthesis of thieno[3,2-b]thiophene [including a catalytic vapour-phase reaction (at 550°C) between 2-(2-thienyl)ethanol and carbon disulfide], its 2-carboxylic acid and its 3,6-dibromo and 2,3,5,6-tetrabromo derivatives are reported. With 2 mol equiv. of butyllithium thieno[3,2-6]thiophene gives its 2,5-dilithiated derivative and its 3,6-dibromo derivative gives the 3,6-dilithiated compound. By quenching with suitable electrophilic reagents these dilithiated compounds have been converted into various 2,5- or 3,6-disubstituted thieno[3,2-6]thiophenes, respectively. Likewise 2,3,5,6-tetrabromothieno[3,2-b]thiophene has been converted into 2,5-disubstituted 3,6-dibromothieno[3,2-b]thiophenes.
- Fuller, Lance S.,Iddon, Brian,Smith, Kevin A.
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p. 3465 - 3470
(2007/10/03)
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- UROKINASE INHIBITORS
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Disclosed are benzothiophene and thienothiophene derivatives useful for inhibiting urokinase activity.
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- 'Cascade' radical reactions in synthesis: Condensed thiophenes from ketenethioacetals
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A novel radical centred tandem cyclisation - tandem fragmentation sequence is described for the direct convertion of ketenethioacetals e.g. 1, 6, 9, 12 and 16 into condensed thiophenes e.g. 2, 7, 10, 13 and 17.
- Harrowven, David C.
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p. 5653 - 5656
(2007/10/02)
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- UREA BASED LIPOXYGENASE INHIBITING COMPOUNDS
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Substituted phenyl, naphthyl, and thienyl N-hydroxy urea compounds form a class of potent inhibitors of 5-and 12-lipoxygenase and are thus useful compounds in the treatment of inflammatory disease states where leukotrienes and other products of lipoxygenase enzyme activity are implicated.
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- New isomeric classes of topically active ocular hypotensive carbonic anhydrase inhibitors: 5-Substituted thieno[2,3-b]thiophene-2-sulfonamides and 5-substituted theio[3,2-b]thiophene-2-sulfonamides
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A series of 5-substituted thieno[2,3-b]- and thieno[3,2-b]thiophene-2-sulfonamides was prepared and evaluated for topical ocular hypotensive activity in glaucoma models. The 5-substituents were varied to maximize both inhibitory potency against carbonic anhydrase and water solubility. At the same time, these substituents were varied in order to obtain compounds with the appropriate pK(a) to minimize pigment binding in the iris. All of these variables were optimized in the best compound, 5-[[(methoxyethyl)](methoxyethyl)ethyl]amino]methyl]thieno[2,3-b] thiophene-2-sulfonamide hydrochloride (55).
- Prugh,Hartman,Mallorga,McKeever,Michelson,Murcko,Schwam,Smith,Sondey,Springer,Sugrue
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p. 1805 - 1818
(2007/10/02)
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- Substituted thieno[3,2-b]thiophene-2-sulfonamides as topically active carbonic anhydrase inhibitors
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Novel substituted thieno[3,2-b]thiophene-2-sulfonamides are prepared by novel synthetic processes. These compounds are useful for the treatment of elevated intraocular pressure in compositions including ophthalmic drops and inserts.
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- SYNTHESIS OF AROMATIC ALDEHYDES VIA 2-ARYL-N,N'-DIACYL-4-IMIDAZOLINES
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Diacylimidazolium ions yield adducts with aromatic compounds.Thus the N,N'-diacetylimidazolium ion and indole gives 1,3-diacetyl-2-(3-indolyl)-4-imidazoline.Less reactive substrates such as thiophene, anisole and 1,3-dimethylbenzene fail to react with this reagent but do form adducts (e.g. 1,3-bis-(trifluoroacetyl)-2-(2-thienyl)-4-imidazoline) with an imidazole/trifluoroacetic anhydride reagent.All of the adducts could be converted to the corresponding aldehyde under mild conditions.The synthetic scope of the new synthesis is similar to that of the Vilsmeier-Haack reaction.
- Bergman, Jan,Renstroem, Lars,Sjoeberg, Birger
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p. 2505 - 2512
(2007/10/02)
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