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ANTITHROMBOTIC AGENTS

This application relates to novel compounds of formula I (and their pharmaceutically acceptable salts), as defined herein, processes and intermediates for their preparation, pharmaceutical formulations comprising the novel compounds of formula I, and the use of the compounds of formula I as thrombin inhibitors.

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Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

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Benzo[b]thiophene Fusion Enhances Local Borepin Aromaticity in Polycyclic Heteroaromatic Compounds

This report documents the synthesis, characterization, and computational evaluation of two isomeric borepin-containing polycyclic aromatics. The syntheses of these two isomers involved symmetrical disubstituted alkynes that were reduced to Z-olefins followed by borepin formation either through an isolable stannocycle intermediate or directly from the alkene via the trapping of a transient dilithio intermediate. Comparisons of their magnetic, crystallographic, and computational characterization to literature compounds gave valuable insights about the aromaticity of these symmetrically fused [b,f]borepins. The fusion of benzo[b]thiophene units to the central borepin cores forced a high degree of local aromaticity within the borepin moieties relative to other known borepin-based polycyclic aromatics. Each isomer had unique electronic responses in the presence of fluoride anions. The experimental data demonstrate that the local borepin rings in these two compounds have a relatively high amount of aromatic character. Results from quantum chemical calculations provide a more comprehensive understanding of local and global aromatic characters of various rings in fused ring systems built upon boron heterocycles.

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Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

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Aminobenzoannulated hetero- and carbocycles from 2-azahepta-2,4-dien-6- ynyllithium compounds: Scope and limitation of a novel benzoannulation reaction

Deprotonation of the N-benzylhetarylmethanimines 9, 12, 15, and 18 at -78C with subsequent warming to room temperature over 16 hours and treatment with electrophiles furnished polysubstituted aminobenzoannulated heterocycles 19-25 in good to excellent yields. In a similar fashion, the deprotonation of the N-allyl-2-(alk-1-ynyl)phenylmethanimines 26 and 27 led to 2-vinylnaphthalen-1-amines 28 and 29, respectively, in moderate yields. The reaction of N-[(trimethylsilyl)methyl]imine 31 afforded naphthalen-1-amine 33, unsubstituted at the ortho position after removal of the trimethylsilyl group. The deprotonation of imine 34, bearing a trimethylsilyl group on the C?C bond, gave none of expected amines, but the substituted imine 35, whose structure was identified using 2D NMR spectroscopy. Georg Thieme Verlag Stuttgart.

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Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

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Palladium(0)-catalyzed Domino C?N Coupling/Hydroamination/C?H Arylation: Efficient Synthesis of Benzothieno[2?,3?:4,5]pyrrolo[1,2-f]phenanthridines

Two new and efficient routes to benzothieno[2?,3?:4,5]pyrrolo[1,2-f]phenanthridines have been developed. Alkynylated benzothiophenes reacted with various anilines to the target compounds in a domino reaction consisting of a C?N coupling-, hydroamination- followed by a final, ring-closing C?H arylation step. Products were isolated in moderate to good yields. (Figure presented.).

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Benzothiophene – Wikipedia,
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A Novel Route to Isoannulated Hetereoaromatic Compounds, 2. – The Dipole Route to Furo/Thieno Pyrroles and alpha-Pyridones, and Their Benzo Derivatives

A new methodology involving 1,7-dipolar cyclizations of conjugated dipoles followed by a multistep rearrangement affording ring-contracted products has been employed for the synthesis of various examples of the title compounds.Under different thermolysis conditions the annulated alkynyl nitrones 15-19, 45, and 46 are converted into isoannulated pyrroles and alpha-pyridones, respectively, with yields up to 90percent (general reaction A –> B + C).The product distribution is strongly influenced by the nature of the thermal substituent R, hence supporting a mechanism with oxo carbenes as central intermediates which undergo either 6-? cyclization to the pyrrole systems or Wolff rearrangement leading to conjugated ketenes, the precursors of the observed alpha-pyridones (see Scheme 1).Diels-Alder reactions were performed with benzofuropyridone 40a, naphthopyridone 62 as well as with the corresponding dihydronaphtho compounds 64a, b.Whereas the tert-butyl derivatives 22b, 23b and 41b are rather unreactive against dienophiles, they are easily transformed into the cyclic imides 31, 32 and 52, respectively, under the influence of oxygen anf light suggesting the formation and subsequent <4 + 2> cycloaddition of 1O2 as important steps. – Key Words: Pyrroles, heteroannulated / alpha-Pyridones, heteroannulated / Pentalenes, dihetero- / Nitrones / Heterocyclizations, 1,7-dipolar / Diels-Alder reactions / Singlet oxygen

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Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

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Photon-Quantitative 6pi-Electrocyclization of a Diarylbenzo[b]thiophene in Polar Medium

The high reactivity of 6pi-electrocyclization in polar solvents has remained one of the important challenges for diarylethenes because of the emergence of a twisted intramolecular charge transfer (TICT) state at the excited state in such polar media, which usually quenches the photocyclization reaction. Herein we report on the preparation and highly efficient photocyclization of 2,3-diarylbenzo[b]thiophenes with nonsymmetric side-aryl units in a polar solvent. While the dithiazolylbenzo[b]thiophene showed a suppressed quantum yield of 6pi-electrocyclization of 54% in methanol, the replacement of a thiazole unit with a thiophene ring led to a photon-quantitative 6pi-cyclization reaction. The nonsymmetrical modification into the side-aryl units was considered to enhance the CH/pi interactions between side-aryl units to support a photoreactive conformation in methanol. The stabilization of the photochromic reactive conformation is expected to suppress the formation of the TICT state at the excited state, leading to highly efficient photoreactivity.

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Benzothiophene – Wikipedia,
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Concise synthesis of highly substituted benzo[a]quinolizines by a multicomponent reaction/allylation/heck reaction sequence

The combination of the recently developed multicomponent construction of highly substituted 3,4-dihydropyridones with subsequent allylation and intramolecular Heck-type cyclization allows the straightforward construction of benzo[a]quinolizines, a class of polycyclic compounds that- despite their interesting pharmacological and photochemical properties- have little precedent in the literature. After optimization of the individual steps, we used this reliable three-step sequence to generate a small library of diversely substituted benzo[a]quinolizines and various heterocyclic analogs. Copyright

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Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

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Dual Gold Catalysis: Bidirectional Processes and Tandem sp3-C?H Insertion Reactions

Various tetrayne systems were converted under dual gold-catalyzed conditions. For symmetric tetraalkynyl-substituted thiophenes, bearing two alkyl-substituted alkynes and two terminal alkyne units, bidirectional cyclizations led to the efficient formation of dibenzothiophene systems. In all cases, selective CH activation of the C?H bond of the alkyl substituent was observed leading to cyclopentane moieties annelated to the newly formed aromatic cores. If two thiophene moieties were tethered over the attached non-terminal alkynes, depending on the length of the connecting alkyl tether, either bidirectional processes or tandem processes can be addressed leading to interesting molecular structures, such as spiro compounds or isolated benzothiophenes connected by a C?C bond. Other electron-rich heterocycles also reacted. While the reactions even worked for some mixed systems, other cases only delivered the products of a mono-cyclization.

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Benzothiophene – Wikipedia,
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Sensitive Assays by Nucleophile-Induced Rearrangement of Photoactivated Diarylethenes

Upon light-induced isomerization, diarylethenes (DAEs) equipped with reactive aldehyde moieties rearrange selectively in the presence of amines, accompanied by decoloration. In a comprehensive study, the probe structure was optimized with regard to its inherent reactivity in the nucleophile-triggered rearrangement reaction. Detailed structure-reactivity relationships could be derived, in particular with regard to the type of integrated (het)aryl moieties as well as the location of the formyl residue, and the probes’ intrinsic reactivity with primary and secondary amines was optimized. Utilizing an ancillary base, the initially formed rearrangement product can engage in a subsequent catalytic cycle, leading to an amplified decoloration process. This additional catalytic pathway allows us to enhance the sensitivity of our method and successfully discriminate between amines and thiols. Moreover, probes that exhibit strong analyte-induced fluorescence modulation have been designed to further decrease the detection limit by using a more sensitive read-out. The optimized DAE probes are promising molecular components for future programmable sensing materials and devices.

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Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

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DIARYLETHENE COMPOUNDS AND USES THEREOF

A compound according to Formula IA and IB, reversibly convertible under photochromic and electrochromic conditions between a ring-open isomer A and a ring-closed isomer B is provided. For substitutent groups, Z is N, O or S; each R1 is independently selected from the group consisting of H, or halo; each R2 is independently selected from the group consisting of H, halo, a polymer backbone, alkyl or aryl; or, when both R2 together form ?CH?CH? and form part of a polymer backbone; each R3 is independently selected from the group consisting of H, halo, alkyl, alkoxy, thioalkyl or aryl; each R4 is aryl; and each R5 is independently selected from the group consisting of H, halo, alkyl, alkoxy, thioalkyl or aryl.

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Reference£º
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem