61341-26-2Relevant articles and documents
Mixed alkylthiophene-based heterocyclic polymers containing oxadiazole units via electrochemical polymerisation: Spectroscopic, electrochemical and spectroelectrochemical properties
Fisyuk, Alexander S.,Demadrille, Renaud,Querner, Claudia,Zagorska, Malgorzata,Bleuse, Joel,Pron, Adam
, p. 707 - 713 (2005)
Symmetric alkylthiophene-based mixed heterocyclic trimer and pentamer. containing central oxadiazole units, have been prepared. Because of the electron-withdrawing properties of oxadiazole, the trimer cannot be electropolymerised and undergoes an oxidative-type destruction at high potentials. In contrast, the pentamer readily polymerises, giving a short chain polymer. Both trimer and pentamer exhibit strong photoluminescence with a maximum at 399 nm (13% quantum yield) and 467 nm (46% quantum yield), respectively. The polymer resulting from the electropolymerisation of the pentamer is also luminescent with the maximum of the excitation band at 528 nm (33% quantum yield). The polymer can be oxidatively doped as demonstrated by cyclic voltammetry, showing a clear anodic peak at 0.62 V versus Ag/Ag + and its cathodic counterpart at 0.56 V, associated with the undoping process. The significantly higher potential of the oxidative doping of the prepared mixed heterocyclic polymer, as compared to the poly(alkylthiophene) homopolymer of similar molecular weight, is caused by the presence of the oxadiazole unit, which lowers the electron density in the π-electron system of the oligothiophene subunit and makes its oxidation more difficult. The spectroelectrochemical investigation of the polymer is consistent with its voltammetric behaviour, exhibiting doping-induced bleaching of the band originating from the π-π* transition and simultaneous growth of the bipolaron bands. The observed clear and reversible spectroelectrochemical behaviour makes the developed polymer a promising candidate for applications in electrochromic devices or electrochemical sensors. The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2005.
A streamlined synthesis of androstadiene C-17 ester derivatives
Gallou, Fabrice,Seeger-Weibel, Manuela,Lupp, Daniel
, p. 877 - 882 (2011)
The development of a fully telescoped synthesis of a derivative of androstadiene C-17 esters made from epoxyparamethasone was demonstrated. This streamlining allowed for the elimination of isolation and solvent change after each synthetic step. Thus it not only drastically reduced the solvent waste, but also minimized the potential exposure to highly active intermediates thereby increasing the overall yield. The intuitively obvious advantage inherent to lowering the number of solvents was illustrated by applying standard green metrics.
Preparation method of thieno[2,3-c]pyridine-7(6h)-ketone
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Paragraph 0034-0035, (2019/04/27)
The invention discloses a preparation method of thieno[2,3-c]pyridine-7(6h)-ketone, belonging to a thienopyridine compound. According to the technical key points, the preparation method comprises thefollowing operation steps of: adding 3-methylthiophene-2-formamide to tetrahydrofuran, then adding DMF-DMA, completely reacting after carrying out heating reflux for 2 to 3 hours, boiling off the tetrahydrofuran and the DMF-DMA under reduced pressured to obtain an oily matter; then adding the oily matter to the tetrahydrofuran, adding alkali in batches, carrying out heating reflux for 1.5-3 hourstill completely reacting, boiling off the tetrahydrofuran, adding 400 to 500ml of water and stirring for 1-2 hours, filtering and drying to obtain the thieno[2,3-c]pyridine-7(6h)-ketone. The preparation method has the beneficial effects that raw materials have relatively low price, the operation steps are simple, and the safety performance in the preparation process is improved.
Pd(II)-Catalyzed Arylation and Intramolecular Amidation of γ-C(sp3)-H Bonds: En Route to Arylheteroarylmethane and Pyrrolidone Ring Annulated Furan/Thiophene Scaffolds
Parella, Ramarao,Babu, Srinivasarao Arulananda
, p. 7123 - 7150 (2017/07/26)
We report the Pd(II)-catalyzed, bidentate directing group (BDG)-assisted arylation and successive arylation/intramolecular amidation of γ-C(sp3)-H bonds. The Pd(II)-catalyzed BDG-assisted C-H activation and functionalization of the β-C(sp3)-H bonds of carboxylic acids are well documented, but only a few reports are available that deal with the BDG-directed functionalization of the γ-C(sp3)-H bonds. Various 3-methylthiophene/furan-2-carboxamides (1a-e) were derived from their corresponding carboxylic acids and bidentate directing groups. These compounds were then used as substrates to investigate the arylation and successive arylation/intramolecular amidation of the γ-C(sp3)-H bonds. The γ-C(sp3)-H arylation arose from the Pd(II)-catalyzed reactions of these compounds with aryl iodides with reaction periods of 4-24 h (except a few reactions which required 36 or 48 h). Notably, these reactions led to the construction of various unsymmetrical diarylmethane scaffolds, such as thiophene/furan-based arylheteroarylmethanes (3-6). Prolonging the reaction period to 48-70 h led to successive γ-C(sp3)-H arylation/intramolecular amidation and the construction of both C-C and C-N bonds. Accordingly, these reactions led to the construction of new classes of pyrrolidone-ring annulated thiophene/furan-based heterocyclic scaffolds (e.g., 4,5-dihydro-6H-thieno[2,3-c]pyrrol-6-ones (8), 4,5-dihydro-6H-furo[2,3-c]pyrrol-6-ones (10), and 1-phenyl-1,2-dihydro-3H-benzo[4,5]thieno[2,3-c]pyrrol-3-ones (12)), and notably, compounds 8, 10, and 12 resemble the skeletons of 3-phenylisoindolin-1-ones.
