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1.
Syntheses and Fluorescent Properties of 6‐Methoxy‐2‐oxoquinoline‐3,4‐dicarbonitriles and 6,7‐Dimethoxy‐2‐oxoquinoline‐3,4‐dicarbonitriles
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Guy Crépin Enoua Günther Lahm Georg Uray Wolfgang Stadlbauer 《Journal of heterocyclic chemistry》2014,51(Z1):E263-E275
4‐Chlorocarbostyrils 3 , 12 , 17 , 24 , 26 with methoxy substituents in 6, 7, or 6,7‐position react with potassium cyanide in a p‐toluenesulfinate mediated reaction either to the highly fluorescent and stable 2‐oxoquinoline‐3,4‐dicarbonitriles 6 , 27 , 29 , 30 or at slightly lower temperatures to 4‐monocarbonitriles 5 , 13 , 18 . 4‐Chlorocarbostyril 3 and lithium p‐toluenesulfinate gave pure 4‐toluenesulfonylquinolone 4 , which reacted with potassium cyanide either to monocarbonitrile 5 or dicarbonitrile 6 , depending on the reaction conditions. 4‐Trifluoromethylquinolones 9 and 19 were prepared for fluorescence comparison from the appropriate methoxyaniline and 4,4,4‐trifluoroacetoacetate. The fluorescence properties such as emission wavelengths and quantum yields of 6‐methoxyderivatives 4 , 5 , 6 , 9 , 13 were studied and compared with those of 7‐methoxy derivatives 18 , 19 and 6,7‐dimethoxyderivatives 27 , 28 , 29 , 30 . 6,7‐Dimethoxy derivatives show best results, showing long‐waved fluorescence spectra up to 520 nm and acceptable quantum yields up to 0.46 for 3,4‐dicyano derivative 27 excited at 440 nm in acetonitrile. 相似文献
2.
On irradiation (λ=350 nm) in the presence of 1,1‐dimethoxyethene, naphthalene‐1,2‐dionemonoacetals 1 regioselectively afford 1,1,4,4‐tetramethoxycyclobuta[a]naphthalen‐3‐ones 3 . Sequential deprotection of these bis‐acetals first lead to 1,1‐dimethoxycyclobuta[a]naphthalene‐3,4‐diones 4 and then to cyclobuta[a]naphthalene‐1,3,4‐triones 6 , which, in turn, are converted into (3,4‐dihydro‐3,4‐dioxonaphthalen‐2‐yl)acetates 7 by treatment with SiO2/MeOH/air. 相似文献
3.
Na Liu Ai‐Ling Cheng En‐Qing Gao 《Acta Crystallographica. Section C, Structural Chemistry》2007,63(2):o93-o95
In 3,4‐di‐2‐pyridyl‐1,2,5‐oxadiazole (dpo), C12H8N4O, each molecule resides on a twofold axis and interacts with eight neighbours via four C—H⋯N and four C—H⋯O interactions to generate a three‐dimensional hydrogen‐bonded architecture. In the perchlorate analogue, 2‐[3‐(2‐pyridyl)‐1,2,5‐oxadiazol‐4‐yl]pyridinium perchlorate, C12H9N4O+·ClO4− or [Hdpo]ClO4, the [Hdpo]+ cation is bisected by a crystallographic mirror plane, and the additional H atom in the cation is shared by the two pyridyl N atoms to form a symmetrical intramolecular N⋯H⋯N hydrogen bond. The cations and perchlorate anions are linked through C—H⋯O hydrogen bonds and π–π stacking interactions to form one‐dimensional tubes along the b‐axis direction. 相似文献
4.
Poly(thieno[3,4‐b]‐1,4‐oxathiane) and poly(3,4‐ethylenedioxythiophene‐co‐thieno[3,4‐b]‐1,4‐oxathiane)/poly(styrene sulfonic sodium): Preparation,characterization, and optoelectronic performance
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Zhipeng Wang Daize Mo Shuai Chen Jingkun Xu Baoyang Lu Qinglin Jiang Zilan Feng Jinhua Xiong Shijie Zhen 《Journal of polymer science. Part A, Polymer chemistry》2015,53(19):2285-2297
In this work, the asymmetrical analog of 3,4‐ethylenedioxythiophene (EDOT), thieno[3,4‐b]‐1,4‐oxathiane (EOTT), was synthesized and chemically polymerized first in aqueous solution using poly(styrene sulfonic sodium) (PSS) as the polyelectrolyte to yield poly(thieno[3,4‐b]‐1,4‐oxathiane) (PEOTT)/PSS. As‐formed film exhibited low electrical conductivity (~10?4 S/cm). Alternatively, EOTT together with EDOT (in different molar ratio of 1:1 and 1:5) was copolymerized and the polymer poly(EOTT‐co‐EDOT)/PSS had electrical conductivity of 10?1 S/cm. After dimethyl sulfoxide (DMSO) treatment, the electrical conductivity was enhanced to 100 S/cm; however, the conductivity of the above homopolymer was reduced (~10?5 S/cm). Raman spectroscopy was used to interpret conductivity enhancement or reduction after DMSO treatment. The conductivity decrease of PEOTT/PSS compared to poly(EOTT‐co‐EDOT)/PSS may arise from the conformational change of PEOTT backbone from the quasi‐planar to the distorted planar mode induced by PSS–/PSSH through ionic interaction. Kinetic studies revealed that the copolymer had high coloration efficiencies (375 cm2/C), low switching voltages (?0.8 to +0.6 V), decent contrast ratios (45%), moderate response time (1.0 s), excellent stability, and color persistence. An electrochromic device employing poly(3‐methylthiophene) and poly(EOTT‐co‐EDOT)/PSS as the anode and cathode materials was also studied. From these results, poly(EOTT‐co‐EDOT)/PSS would be a promising candidate material for organic electronics. © 2015 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2015 , 53, 2285–2297 相似文献
5.
Rüdiger Faust Clemens Bruhn Sara Rossi 《Acta Crystallographica. Section C, Structural Chemistry》2005,61(4):o253-o255
The structure of bis(4‐tert‐butyl‐2,6‐dimethylphenyl)hexa‐1,5‐diyne‐3,4‐dione, C30H34O2, has been determined, revealing an extended s‐trans conformation of the dione and the two ynone moieties, which are shielded by the flanking methyl substituents. The structural parameters and the packing arrangement suggest little electronic delocalization between the two ynone moieties. 相似文献
6.
Thieno[3,4‐c]pyrrole‐4,6‐dione‐3,4‐difluorothiophene Polymer Acceptors for Efficient All‐Polymer Bulk Heterojunction Solar Cells
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Dr. Shengjian Liu Dr. Zhipeng Kan Dr. Simil Thomas Federico Cruciani Prof. Jean‐Luc Brédas Prof. Pierre M. Beaujuge 《Angewandte Chemie (International ed. in English)》2016,55(42):12996-13000
Branched‐alkyl‐substituted poly(thieno[3,4‐c]pyrrole‐4,6‐dione‐alt‐3,4‐difluorothiophene) (PTPD[2F]T) can be used as a polymer acceptor in bulk heterojunction (BHJ) solar cells with a low‐band‐gap polymer donor (PCE10) commonly used with fullerenes. The “all‐polymer” BHJ devices made with PTPD[2F]T achieve efficiencies of up to 4.4 %. While, to date, most efficient polymer acceptors are based on perylenediimide or naphthalenediimide motifs, our study of PTPD[2F]T polymers shows that linear, all‐thiophene systems with adequately substituted main chains can also be conducive to efficient BHJ solar cells with polymer donors. 相似文献
7.
Michael J. Bayer Hans Pritzkow Walter Siebert 《Acta Crystallographica. Section C, Structural Chemistry》2003,59(5):o257-o258
In the title compound, 1,1,6a,7,9a,10‐hexachloro‐2,3,5,6,8,9,11,12‐octa‐p‐tolyl‐1,6a,9a,12a‐tetraborata‐3a,4a,7,10‐tetrabora‐4a1,6b,9b,12b‐tetraoxonia‐4‐oxatetracyclopenta[1,2‐a:2,1,5‐de:1,2‐g:1,2‐i]naphthalene dichloromethane pentasolvate, C64H56B8Cl6O5·5CH2Cl2, two condensed oxadiborole rings are attached to two further oxadiborole rings in a type of donor–acceptor bonding, thus forming a ten‐membered alternating (B—O)5 naphthalene‐like arrangement as the central building block. 相似文献
8.
Tsonko Kolev Denitsa Yancheva Boris Shivachev Rosica Petrova Michael Spiteller 《Acta Crystallographica. Section C, Structural Chemistry》2005,61(4):o213-o215
The title compound, C16H9NO4, also known as the 3‐benzoylpyridinium betaine of squaric acid, exhibits a dipolar electronic ground‐state structure with a positively charged pyridinium fragment and a negatively charged squarate moiety. In the molecule, the two aromatic rings are twisted by 56.03 (2)° relative to one another. The three‐dimensional packing of the molecules is stabilized by C—H·O short contacts. 相似文献
9.
The condensation of 4‐amino‐5‐mercapto‐3‐(5‐methylisoxazol‐3‐yl)‐1,2,4‐triazole with substituted phenacyl bromide, aldehydes, p‐bromophenylisothiocyanate, aromatic carboxylic acids and oxalic acid, is described. The antibacterial activity of representative compounds was evaluated. 相似文献
10.
Heong‐Seup Yim Ho‐Kyun Kim Jeum‐Jong Kim Deok‐Heon Kweon Yong‐Jin Yoon Sang‐Gyeong Lee Jung‐Ho Kim 《Journal of heterocyclic chemistry》2007,44(4):909-914
11.
A. Kakanejadifard A. Saniei F. Delfani M. Farnia G. R. Najafi 《Journal of heterocyclic chemistry》2007,44(3):717-718
12.
Synthesis of Polysubstituted Pyrazolo[3,4‐b]pyridine‐3‐Carbohydrazide and Pyrazolo[3,4‐d]pyridazine Derivatives
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Dinesh C. Bhavsar Prashant S. Nikam Sachin A. Gangurde Raghunath B. Toche 《Journal of heterocyclic chemistry》2014,51(3):635-641
5‐Amino‐4‐formyl pyrazole carboxylate gave facile reactions with malononitrile, hydrazine, and ketones in the presence of piperidine furnished substituted pyrazolo[3,4‐b]pyridines and pyrazolo[3,4‐b]quinolones. The pyridazine sulfonamides were obtained by the reaction of 5‐chloro 4‐formyl pyrazole carboxylate with sulfonamide derivatives. 相似文献
13.
《Journal of heterocyclic chemistry》2017,54(4):2434-2439
A domino three‐component strategy with high efficiency for the synthesis of spiro[indoline‐3,4′‐pyrazolo[3,4‐b ]pyridines] from easily available isatins, pyrazol‐5‐amines and β‐ketonitriles under microwave heating. During reaction process, HOAc plays dual roles as reaction media as well as a Brønsted acid‐promoter. Flexible structural modification, broad functional group compatibility and mild reaction conditions make this strategy a useful and attractive process of library generation for drug discovery. 相似文献
14.
Starting from 1‐[(tert‐butoxy)carbonyl]piperidine‐4‐carboxylic acid and 2‐bromoaniline, the spiro[indole‐3,4′‐piperidin]‐2‐one system was obtained in three high‐yielding steps: anilide formation, N(1)‐protection, and intramolecular cyclization under Pd catalysis as the key reaction. The preparation of the corresponding 2‐bromoanilide was studied. In extension, the same sequence was developed with 4‐methyl‐ and 4‐nitro‐2‐bromoaniline. In the key step, the NO2 group led to a rather diminished yield. The transformation of the protected spiro[indole‐3,4′‐piperidin]‐2‐one to the corresponding unprotected dihydroindoles is discussed. 相似文献
15.
Ahmad Shaabani Fatemeh Hajishaabanha Hamid Mofakham Mojtaba Mahyari Bagher Lali 《Helvetica chimica acta》2012,95(2):246-254
A novel and efficient isocyanide‐based multicomponent reaction between alkyl or aryl isocyanides 1 , 2,3‐diaminomaleonitrile ( 2 ), naphthalene‐2,3‐diamines ( 6 ) or benzene‐1,2‐diamine ( 9 ), and 3‐oxopentanedioic acid ( 3 ) or Meldrum's acid ( 4 ) or ketones 7 was developed for the ecologic synthesis, at room temperature under mild conditions, of 1,6‐dihydropyrazine‐2,3‐dicarbonitriles 5a – 5f in H2O without using any catalyst, and of 3,4‐dihydrobenzo[g]quinoxalin‐2‐amine and 3,4‐dihydro‐3,3‐dimethyl‐quinoxalin‐2‐amine derivatives 8a – 8g and 10a – 10e , respectively, in the presence of a catalytic amount of p‐toluenesulfonic acid (TsOH) in EtOH, in good to excellent yields (Scheme 1). 相似文献
16.
Ondřej Rudolf Michal Rouchal Antonín Lyčka Antonín Klásek 《Helvetica chimica acta》2013,96(10):1905-1917
3‐Alkyl/aryl‐3‐hydroxyquinoline‐2,4‐diones were reduced with NaBH4 to give cis‐3‐alkyl/aryl‐3,4‐dihydro‐3,4‐dihydroxyquinolin‐2(1H)‐ones. These compounds were subjected to pinacol rearrangement by treatment with concentrated H2SO4, resulting in 4‐alkyl/aryl‐3‐hydroxyquinolin‐2(1H)‐ones. When a benzyl (Bn) group was present in position 3 of the starting compound, its elimination occurred during the rearrangement, and the corresponding 3‐hydroxyquinolin‐2(1H)‐one was formed. The reaction mechanisms are discussed for all transformations. All compounds were characterized by IR, 1H‐ and 13C‐NMR spectroscopy, as well as mass spectrometry. 相似文献
17.
Maria J. Malankiewicz 《Journal of heterocyclic chemistry》2000,37(4):697-702
Reaction of 4‐chloro‐3′‐methylthio‐3,4′‐diquinolinyl sulfides 3, 9b, 9c with a nitrating mixture proceeds via the 3′‐methylthio group monooxidation and yields 3′‐methylsulfinyl diquinolinyl sulfides 4, 5b, 5c , respectively. Further treatment of 4 with a nitrating mixture followed as C5‐ and C8‐nitration and gives mixture of 5a and 5c. Treatment of 3′‐methylsulfinyl quinolines 6 and 7 with hydrochloric acid/potassium iodide system causes reduction of the sulfoxide group in 6 and 7 to the sulfide group yielding 8 , in case of 4‐methoxyquinolines 6 , hydrolysis of the 4‐methoxyquinoline moiety to the 4‐quinolinone moiety takes place simultaneously. The proton and carbon chemical shifts of 4 and 5a were completely assigned following COSY, HETCOR and INEPT or COLOC studies. 相似文献
18.
Pavel Hradil Lubomír Kvapil Jan Hlav
Tom Weidlich Antonín Ly
ka Karel Lemr 《Journal of heterocyclic chemistry》2000,37(4):831-837
The cyclization of phenacyl anthranilate has been studied with the aim to develop the synthesis of 2‐(2′‐aminophenyl)‐4‐phenyloxazole. However, a different course of the reaction than expected was observed. 2‐Phenyl‐2‐hydroxymethyl‐4‐oxo‐1,2,3,4‐tetrahydroquinazoline ( 3a ) was formed by the reaction of phenacyl anthranilate ( 2 ) with ammonium acetate under various conditions. 3‐Hydroxy‐2‐phenyl‐4(1H)‐quinolinone ( 4 ) arose by heating compound 3a in acetic acid. The same compound was obtained by melting compound 3a , but the yield was lower. Different types of products resulted in the reaction of compound 3a with acetic anhydride. Under mild conditions acetylated products 2‐acetoxymethyl‐2‐phenyl‐4‐oxo‐1,2,3,4‐tetrahydroquinazoline ( 7a ) and 2‐acetoxymethyl‐3‐acetyl‐2‐phenyl‐4‐oxo‐1,2,3,4‐tetrahydroquinazoline ( 8 ) were prepared. If the reaction was carried out under reflux of the reaction mixture, molecular rearrangement took place to give cis and trans 2‐methyl‐4‐oxo‐3‐(1‐phenyl‐2‐acetoxy)vinyl‐3,4‐dihydroquinazolines ( 9a and 9b ). All prepared compounds have been characterised by their 1H, 13C and 15N NMR spectra, IR spectra and MS. 相似文献
19.
H. D. Hollis Showalter Anthony D. Sercel Michael A. Stier William R. Turner 《Journal of heterocyclic chemistry》2001,38(4):961-964
Approaches toward the preparative‐scale synthesis of target 3,4‐dihydro‐1(2H)‐isoquinolinones 1–3 are presented. Compounds 1 and 2 were prepared via a Schmidt rearrangement on easily obtained indanone precursors, but in low overall yield. A better method to make this class of compounds is exemplified by the large‐scale synthesis of 2 via a Curtius rearrangement sequence. Thus, high‐temperature thermal cyclization of an in situ formed styryl isocyanate from precursor 8 in the presence of tributylamine gave the corresponding 1(2H)‐isoquinolinone ( 9 ). Catalytic hydrogenation of 9 provided the desired 3,4‐dihydro‐5‐methyl‐1(2H)‐isoquinolinone ( 2 ) in 65 % overall yield. Similar reduction of a commercially available 5‐hydroxy‐1(2H)‐isoquinolinone precursor 10 followed by an O ‐alkylation/amination sequence gave target 3 in good overall yield. The route proceeding via the Curtius rearrangement is recommended for large scale synthesis of other 3,4‐dihydro‐1(2H)‐isoquinolinones. Only when deactivating substituents or sensitive functionality within the benzenoid ring render the high temperature ring closure of the intermediate isocyanate inefficient might a Schmidt rearrangement protocol be the method of choice. 相似文献
20.
Victor V. Turytsya Yuri V. Ostapiuk Vasyl V. Matiychuk Mykola D. Obushak 《Journal of heterocyclic chemistry》2014,51(6):1898-1901
3‐Substituted methyl 3,4‐dihydroisocoumarin‐6‐carboxylates were obtained by the intramolecular cyclization of 2,5‐dimethoxycarbonyl benzenediazonium bromides with methyl/ethyl acrylate and styrenes under Meerwein's arylation conditions. 相似文献