共查询到20条相似文献,搜索用时 15 毫秒
1.
Larisa N YudinaJan Bergman 《Tetrahedron》2003,59(8):1265-1275
Double Fischer cyclisation was used to prepare indolo[3,2-b]carbazole and its 2,8-di-OMe, OH, Br and F-derivatives. N-monosubstituted derivatives of indolo[3,2-b]carbazole (methyl, hydroxymethyl, dimethylaminoethyl) were obtained starting from 5,11-di-Boc-indolo[3,2-b]carbazole. 相似文献
2.
He-ping Shi Li-wen ShiJian-xin Dai Lei XuMei-hua Wang Xiao-huan WuLi Fang Chuan Dong Martin M.F. Choi 《Tetrahedron》2012,68(47):9788-9794
Three novel indolo[3,2-b]carbazoles derivatives were successfully synthesized by condensation reaction and structurally characterized by elemental analysis, mass spectrometry and proton nuclear magnetic resonance spectroscopy methods, which belong to donor-π-acceptor systems comprising an indolo[3,2-b]carbazole group as an electron donor and two benzothiazole rings as electron acceptors. The thermal, electrochemical and photophysical properties of the compounds were characterized by thermogravimetric analysis combined with electrochemistry, UV-vis absorption spectroscopy and fluorescence spectroscopy. On the other hand, the geometries, molecular orbitals, charge-injection and transport properties were determined by quantum chemical calculations. The results show that the compounds synthesized exhibit good thermal stability and high fluorescence quantum yields, indicating the potential application as optoelectronic materials. 相似文献
3.
Roman A. Irgashev Anton Yu. Teslenko Ekaterina F. Zhilina Aleksandr V. Schepochkin Oleg S. El'tsov Gennady L. Rusinov Valery N. Charushin 《Tetrahedron》2014
Novel 5,11-dialkyl-6,12-di(thiophen-2-yl) substituted 5,11-dihydroindolo[3,2-b]carbazoles have been obtained and plausible ways for their further modifications via the Friedel–Crafts reaction are presented. The formylation of these indolo[3,2-b]carbazoles with dichloromethyl alkyl esters catalysed by Lewis acids leads to the formation of the corresponding 2,8-diformyl derivatives. Applicability of this formylation method for modification of indolo[3,2-b]carbazoles bearing electron-rich aromatic substituents at C-6 and C-12 has also been demonstrated. The Knoevenagel condensation of 2,8-dialdehydes with active methylene nitriles has been studied. The measurements of optical and redox properties for a number of new indolo[3,2-b]carbazoles have been performed. 相似文献
4.
Junting Yu Jian LuoQing Chen Keqi HeFanyuan Meng Xianping DengYafei Wang Hua Tan Haigang JiangWeiguo Zhu 《Tetrahedron》2014
A novel bi-picolinic acid derivative of H2dipic-BTICz containing binary triphenylamine-substituted indolo[3,2-b]carbazole (BTICz) unit and its dinuclear platinum(II) complex of (dfppy)2Pt2(dipic-BTICz) were synthesized as a single-component emitter used in the white polymer light-emitting diodes (WPLEDs), where dfppy is 2-(2,4-difluorophenyl)pyridine and dipic-BTICz is an anion of H2dipic-BTICz. The photophysical and electrochemical properties of (dfppy)2Pt2(dipic-BTICz) were investigated. Compared with the reported mononuclear platinum complex of (dfppy)Pt(pic), (dfppy)2Pt2(dipic-BTICz) exhibited a red-shifted photoluminescent peak at 434 nm in dilute dichloromethane (10−5 M), but a weakened and red-shifted aggregation emission peak at 640 nm besides its intrinsic emission at 445 nm in its neat films. Stable pure white emissions with CIE coordinates of (0.325±0.005, 0.345±0.015) and a maximum brightness of 208 cd/m2 were observed in the (dfppy)2Pt2(dipic-BTICz)-doped single-emissive-layer (SEL) PLEDs using a blend of poly(vinylcarbazole) and 2-(4-biphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole as a host matrix at 1 wt % dopant concentrations under applied voltages from 9 to 14 V. It indicates that the intrinsic and aggregation emissions of this dinuclear platinum complex were effectively tuned by inserting a new BTICz fluorophore in the dual picolinic acid derivative. Therefore, it is a promising single-component emitter to get white emission in SEL PLEDs. 相似文献
5.
Reduction of indolo[2,3-b]quinoxalines with zinc in the presence of an anhydride gave N,N-diacyl trapped 6,11-dihydroindolo[2,3-b]quinoxalines in 43-92% yields. When the reduction with zinc was performed in TFA/TFAA, an unexpected ring opened product was isolated in 49% yield. The structure of this product could be identified as 1,2-dihydro-1-trifluoroacetyl-3-[(2-trifluoroacetylamino)phenyl]quinoxaline. 相似文献
6.
Makhluf J. Haddadin Claudia El-Nachef Yara Chaaban James C. Fettinger 《Tetrahedron letters》2010,51(51):6687-6689
Synthesis of the strained 2H-thieto[3,2-b]quinoline ring system is reported for the first time. Treatment of (Z)-2-benzyliden-2H-thieto[3,2-b]quinoline derivatives of this heterocycle with base, at reflux in ethanol, causes a novel rearrangement to 2-phenylthieno[3,2-b]quinolines. Indeed, the one-pot reaction of 2-aminobenzaldehydes and (Z)-2-benzylidenethietan-3-one in refluxing basic ethanol leads directly to 2-phenylthieno[3,2-b]quinolines in good yields. 相似文献
7.
Niyaz A. Mir Tariq A. Shah Sarfaraz Ahmed M. Muneer Nigam P. Rath Musheer Ahmad 《Tetrahedron letters》2014
A series of imidazo[2,1-b]thiazole and benzo[d]thiazolo[3,2-a]imidazole analogues were synthesized by stirring an equimolar mixture of dibenzoylacetylene with imidazole/thiazole derivatives in toluene or acetonitrile at room temperature. The products were generated in good yields and characterized by standard analytical techniques such as IR, 1H NMR, 13C NMR and mass spectrometry. The structure of products 19, 20, 22, 24 and 25 were also unambiguously confirmed by single crystal X-ray analysis. 相似文献
8.
Subburethinam RameshRajagopal Nagarajan 《Tetrahedron letters》2011,52(38):4857-4860
An efficient and convenient one-pot intramolecular aza Diels-Alder approach for the synthesis of dihydrochromeno[4,3-b]pyrrolo[3,2-f]quinolines has been reported. Particularly valuable features of this methodology include simple execution, inexpensive catalyst, and good product yields. 相似文献
9.
Shigeo Tohyama 《Tetrahedron letters》2005,46(32):5263-5264
A new total synthesis of calothrixin B is described. The key step is an allene-mediated electrocyclic reaction involving the indole 2,3-bond for the construction of a suitable 4-oxygenated 2,3,4-trisubstituted carbazole ring system. 相似文献
10.
Akira Yamabuki 《Tetrahedron letters》2006,47(33):5859-5861
A biomimetic approach to calothrixin B via a hypothetical metabolite, 6-formylindolo[2,3-a]carbazole, is described. The construction of a suitable indolo[2,3-a]carbazole ring system was carried out using an allene-mediated electrocyclic reaction involving two [b]-bonds of indoles as the key step. 相似文献
11.
New organic dyes containing indolo[2,3-b]quinoxaline donor have been synthesized for application in dye sensitized solar cells as sensitizers. The dyes exhibited interesting optical properties tuneable by the nature of the conjugation bridge. Origin of the optical transitions in the dyes was corroborated by the TDDFT computations. The LUMO and HOMO of the dyes were found to be favourable for electron injection into the conduction band of TiO2 and the regeneration of the dye by the redox shuttle in the electrolyte, respectively. Since the dyes exhibited solvent dependent absorption properties, DSSC were fabricated from two different dye bath solutions, DCM and acetonitrile/tert-butanol/dimethylsulphoxide mixture. The dyes adsorbed from the later bath solution led to better device performance owing to the comparatively less charge transfer resistance arising from the well-spaced dye packing. Among all dyes, a dye containing thiophene in the π-spacer exhibited the highest device efficiency. 相似文献
12.
An efficient synthesis of 3-amino-6-bromofuro[3,2-b]pyridine-2-carboxamides is described via the formation of 3-amino-6-bromofuro[3,2-b]pyridine-2-carbonitrile. Functionalization of the amino group at position 3 of the heterocycle will be discussed. 相似文献
13.
A series of new substituted triphenylamine (TPA) derivatives with alkyl thieno[3,2-b]thiophene and thiophene units were synthesized in a combinatorial manner. Suzuki coupling of a dioxaborolane TPA derivative and 2-bromo-3-nonylthieno[3,2-b]thiophene or Stille coupling of fresh stannyl thieno[3,2-b]thiophene was used. All compounds were characterized by 1H and 13C NMR, HRMS, UV-vis spectrometry and DSC measurements. It was demonstrated that the optical and thermal properties of these materials can be tuned by varying both the conjugation length and thienothiophene and thiophene combination on the TPA branches. Moreover, the measured molar extinction coefficients were increasing from 63,000 (λmax = 354 nm) to 131,000 L mol−1 cm−1 (λmax = 428 nm) for TPA-thienothiophenes and TPA-bithiophene thienothiophenes, respectively. Some of them showed molecular glass behavior. 相似文献
14.
Ricardo C. Calhelha 《Tetrahedron letters》2010,51(2):281-283
Two methyl 3-aminothieno[3,2-b]pyridine-2-carboxylates were prepared from 3-fluoro or 3-nitropicolinonitriles and methyl thioglycolate in DMF/KOH(aq). From the unsubstituted precursor in the pyridine ring, di(hetero)arylamines were obtained by C-N Buchwald-Hartwig coupling with bromonitrobenzenes and with 2-bromopyridine. In the latter case a tetracyclic compound was formed by intramolecular cyclization. Using a brominated derivative in the pyridine ring as a coupling component, it was possible to synthesize C-C (Suzuki and Sonogashira) and C-N (Buchwald-Hartwig) coupling products and a tetracyclic compound obtained by bifunctionalization of the thienopyridine system. 相似文献
15.
Laure Biniek Ibrahim BulutPatrick Lévêque Thomas HeiserNicolas Leclerc 《Tetrahedron letters》2011,52(15):1811-1814
New indolo[2,3-a][1,2,5]thiadiazolo[3,4-c]carbazoles including functional groups (halide or hydroxyl groups) on the meta positions relative to the nitrogen atoms which are known to be the most conjugated, have been synthesized following two synthetic routes. The characterizations of their optical and electrochemical properties evidence their potential as new building blocks for optoelectronic materials. 相似文献
16.
Suitably functionalized 3-carbomethoxy/cyano-2H-pyran-2-ones are excellent synthons for the synthesis of arenes and heteroarenes of therapeutic importance. The compounds 6-aryl-3-cyano-4-methylsulfanyl-2H-pyran-2-ones have been transformed into bridgedhead azolopyrimidines and imidazothiazines through thermal and base-induced ring transformation reactions with aminoazoles and imidazolidin-2-thiones, respectively. 相似文献
17.
Vegar Stockmann 《Tetrahedron》2008,64(32):7626-7632
Two new types of pyrido-fused tris-heterocycles (1a,b and 2a,b) have been prepared from 3-aminopyridine in five/six steps. A synthetic strategy for the preparation of the novel pyrido[3,4-b]thieno[2,3- and 3,2-d]pyrroles (1a,b) and pyrido[4,3-e]thieno[2,3- and 3,2-c]pyridazines (2a,b) has been studied. The Suzuki cross coupling of the appropriate 2- and 3-thienoboronic acids (3,4) and 4-bromo-3-pyridylpivaloylamide (9) afforded the biaryl coupling products (10,11) in high yields (85%). Diazotization of the hydrolysed (2-thienyl)-coupling product (12) and azide substitution gave the 3-azido-4-(2-thienyl)pyridine intermediate (72%, 14). 3-Azido-4-(3-thienyl)pyridine (15) was prepared by exchanging the previous order of reactions. The desired β-carboline thiophene analogues (1a,b) were obtained via the nitrene by thermal decomposition of the azido precursors (14,15). By optimising conditions for intramolecular diazocoupling, the corresponding pyridazine products (72-83%, 2a,b) were afforded. 相似文献
18.
Anne BretéchéPascal Marchand Marie-Renée NourrissonPatrick Hautefaye Guillaume De NanteuilMuriel Duflos 《Tetrahedron》2011,67(26):4767-4773
The synthesis of novel functionalized 3-amino-N-methylfuro[3,2-b]pyridine-2-carboxamides is described from cyanopyridine intermediates. Based on the difference in halogen reactivity, ethyl [(5-bromo-2-chloropyridin-3-yl)oxy]acetate was functionalized by a palladium-catalyzed reaction, before the cyclization to the desired furo[3,2-b]pyridines. 相似文献
19.
A new indoloquinazoline alkaloid, ophiuroidine 1, having an indolo[2,1-b]quinazoline-6,12-dione skeleton, was isolated from the Caribbean ophiuroid, Ophiocoma riisei. The structure of 1 was determined as 4,8,9-trihydroxyindolo[2,1-b]quinazoline-6,12-dione from spectroscopic data. Ophiuroidine 1 is the first example of an indoloquinazoline alkaloid found in a marine invertebrate. 相似文献
20.
Kengo Asai Yumiko Nakajima Fumiyuki Ozawa 《Journal of organometallic chemistry》2011,696(6):1266-1243
Silylethynyl-substituted oligothiophenes and thieno[3,2-b]thiophene were synthesized by the Sonogashira coupling reaction. The absorption and fluorescence maxima of these compounds shifted to longer wavelength, and they exhibited higher absorption coefficients and quantum yields than the corresponding unsubstituted molecules and tert-butylethynyl derivatives. From the DFT calculation, the energy band gap between HOMO and LUMO decreases by the introduction of a silicon atom. Thus, silyl groups can play important role in enhancing the quantum efficiency and decreasing the band-gap of chromophores. Hence, Silylethynyl group can serve as a highly efficient auxiliary for use in optical devices. 相似文献