Synthesis and Crystal Structure of 2,10-Di-tert-butylindolo[3,2,1-jk]carbazole

The title compound, 2,10-di-tert-butylindolo[3,2,1-jk]carbazole (C26H27N, Mr=353.49), has been synthesized by palladium-catalyzed intramolecular arylation and characterized by 1H NMR, 13C NMR and X-ray crystal structure determination. The crystal crystallizes in the monoclinic system, space group P21/c with a=13.6409(5), b=11.6706(4), c=13.1678(5), β=100.6180(10)°, V=2060.39(13)3 , Z=4, Dc=1.140 mg/m3 , μ=0.065mm-1 , F(000)=760, the final R=0.0456 and wR=0.1209 for 3012 observed reflections (I > 2σ(I)).     

Synthesis and structures of two novel indolo[3,2-b] carbazole derivatives

Indolocarbazole derivatives have already been reported to be good organic semiconductor candidates. The knowledge of the relationship between the structure and packing of molecules in crystal is indispensable in design of high performance organic semiconductor materials. Two new indolocarbazole derivatives, 2,8-dibromo-5,11-di-[4-(isoindole-1,3-dione-2-yl)butyl]indolo[3,2-b]carbazole (I) and 2,8,6,12-tetrabromo-5,11-di-(4-chlorobutyl)indolo[3,2-b]carbazole (II) have been synthesized and the crystal structures have been studied. The dichloromethane solvate of (I), C₄₂H₃₂Br₂N₄O₄ · 2CH₂Cl₂, is monoclinic, space groups P2₁/n. Unit cell parameters are a = 11.6847(2), b = 12.6942(2), c = 13.7899(2) Å, β = 91.8220(10)°. Unlike other indolo[3,2-b]carbazole derivatives, there is no any π–π stacking between the indolocarbazole backbone of two adjacent molecules in the crystal. Since the isoindole-1,3-dione-2-yl is introduced in 5- and 11-positions in the molecule, the intermolecular short contacts mainly localize in between the pendant groups of the neighboring indolocarbazole molecules. The compound (II) is also monoclinic with P2₁/c space groups. Unit cell parameters are a = 4.6427(9), b = 11.425(2), c = 24.511(4) Å, β = 93.47(1)°. In contrast with compound (I), the molecules of (II) possess strong face-to-face π–π stacking. The crystal structures were studied in detail. It is concluded that linear pedant groups benefit to co-facial π–π interaction. Additionally, the molecule electronic spectra were studied by quantum chemistry theoretical calculation.     

吲哚并咔唑类衍生物载流子传输性质的理论研究

以密度泛函理论结合跳跃模型, 重点研究了氯原子和烷基链的引入对吲哚并咔唑类衍生物传输性质的影响. 计算结果表明, 与吲哚并[3,2-b]咔唑(1)相比, 氯原子的引入增大了2,8-二氯吲哚并[3,2-b]咔唑(2)和2,8-二氯-5,11-二己基吲哚并[3,2-b]咔唑(3)的最高占据分子轨道(HOMO)的离域程度, 而对最低未被占据分子轨道(LUMO)则无显著贡献, 但明显降低了二者的能级. 上述结果表明, 对于LUMO, 氯原子体现了吸电子效应, 而对于HOMO, 氯原子体现了共轭效应. 烷基链的引入使化合物3的空穴迁移率明显高于化合物1和2, 这主要归因于化合物3具有更加紧密的分子堆积, 尤其在跳跃路径A中, 具有更大的分子间电子耦合和轨道重叠. 同时能带结构的计算结果进一步证明, 氯原子和烷基链的同时引入大大改善了吲哚并咔唑类衍生物的电荷传输性能.     

Synthesis and Crystal Structure of 7-Ethoxycarbonyl-2-methyl-6-methylthio-lH-imidazo[1,2-b]pyrazole

The title compound 7-ethoxycarbonyl-2-methyl-6-methylthio-1H-imidazo[1,2-b]-pyrazole (Mr = 239.29) was synthesized and structurally characterized by IR, 1H NMR and single-crystal X-ray diffraction. It belongs to the triclinic system, space group P1, with a = 8.0461(10), b = 8.5534(11), c = 9.5605(12) A, α = 64.804(2), β = 74.231(2), γ = 76.885(2)°, V= 568.27(12) A3, Z = 2, Dc = 1.398 g/cm3,μ= 0.274 mm-1, F(000) = 252, the final R.= 0.0454 and wR = 0.1261. A total of 3360 reflections were collected, of which 2466 were independent (Rint = 0.0138) and 2154 were observed with I > 2σ(Ⅰ).     

Synthesis and Crystal Structure of exo-4-（3,4-Dichlorophenyl）-8-ethyl-3,3a,4,5,8, 12d-hexahydro-2H-furo[3,2-c]indolo[3,2-f]quinoline

The title compound exo-4-(3,4-dichlorophenyl)-8-ethyl-3,3a,4,5,8,12d-hexahydro-2H-furo[3,2-c]indolo[3,2-f]quinoline (C25H22Cl2N2O, Mr = 437.35) was synthesized and crystallized. The crystal belongs to tetragonal, space group I4(1)/a with a = 17.4903(3), b = 17.4903(3), c = 28.3403(5) , Z = 16, V = 8669.6(3) 3, Dc = 1.340 g·cm-3, μ(MoKɑ) = 0.319 mm-1, F(000) = 3648, R = 0.0429 and wR = 0.711 for 2714 observed reflections I > 2σ(I). X-ray analysis reveals that atoms C(1), C(2), C(3), C(4), C(5) and N(1) on the new pyridine ring are slightly distorted, forming a distorted boat conformation.     

Synthesis and Crystal Structure of 7-Ethoxycarbonyl-2-methyl-6-methylthio-1H-imidazo[1,2-b]pyrazole

The title compound 7-ethoxycarbonyl-2-methyl-6-methylthio-lH-imidazo[1,2-b]- pyrazole （Mr = 239.29） was synthesized and structurally characterized by IR, ^1H NMR and single-crystal X-ray diffraction. It belongs to the triclinic system, space group P1, with a =8.0461（10）, b = 8.5534（11）, c = 9.5605（12）А,α= 64.804（2）,β= 74.231（2）, γ= 76.885（2）°, V = 568.27（12）А^3, Z = 2,Dc= 1.398 g/cm^3,μ= 0.274 nunl, F（000） - 252, the final R = 0.0454 and wR = 0.1261. A total of 3360 reflections were collected, of which 2466 were independent （R_int = 0.0138） and 2154 were observed with I〉2σ（I）.     

Synthesis,Crystal Structure and Cytotoxic Activity of a New N-Vinyl-1H-dibenzo[a,c]carbazole Derivative of the Dehydroabietic Acid

The title compound （C29H33NO2, 3） was synthesized and structurally characterized by elemental analysis, IR, MS, 1H- and 13C-NMR and single-crystal X-ray diffraction. The crystal is of monoclinic system, space group P21 with a = 14.428（3）, b = 7.3440（15）, c = 22.768（5） A, β = 95.17（3）°, V = 2402.7（8） A3, Z = 4, Mr = 427.56, Dc = 1.182 g/cm3, F （000） = 920, 2（MoKa） = 0.71073 A,μ = 0.073 mm-1, the final R= 0.0670 and wR= 0.1002 for 2437 reflections with I〉 2σ（I） Two crystallographically independent molecules with different conformations co-exist in the structure. The crystal structure is stabilized by intermolecular C-H…π interactions which make the molecules stack along the b axis. In addition, the preliminary cytotoxic assay showed that the title compound exhibited moderate inhibitory activity against KB and SW1116 cells.     

Synthesis and Crystal Structure of 3-Benzyl-6-trichloromethyl-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole

The title compound 3-benzyl-6-trichloromethyl-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole I （C11HTC13N4S, Mr = 333.62） has been synthesized, and its structure was determined by elemental analyses, IR, ^1H NMR, ^13C NMR, and X-ray diffractions. The crystal is of triclinic, space group P1^-, with a = 5.898（3）, b = 10.510（4）, c = 11.580（5） A, α = 74.936（7）, β= 75.476（7）, γ = 79.647（7）°, V= 665.9（5）/A^3, F（000） = 336, Z= 2, Dc = 1.664 g/cm^3, 2 = 0.71073A, p = 0.834 mm^-1, the final R = 0.0605 and wR = 0.0900. The secondary bonding interactions （SBIs） S…N and π-π stacking interactions are found in the crystal structure and they link the molecules into a three-dimensional network.     

新型咔唑衍生物的合成及其晶体结构

通过9-乙基咔唑-3-甲醛与4-氨基-3,5-二甲基-1,2,4-三氮唑反应,合成了一种新型咔唑衍生物-- 9-乙基咔唑-3-甲醛缩4-氨基-3,5-二乙基-1,2,4-三氮唑(1),其结构经1H NMR, IR和X-射线单晶衍射表征.1属单斜晶系,P2(1)/n空间群,晶胞参数为:a=8.829(8)(A), b=9.863(10)(A), c=19.530(15)(A), β=101.65(5)°, V=1 666(3)(A)3, Dc=1.266 g·cm-3, Z=4, F(000)=672, μ=0.079 mm-1.最终偏离因子R1=0.075 6.     

Synthesis,Characterization and Crystal Structure of 3-o-Fluorophenyl-6-（4-decarboxydehydroabietyl）-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazole

Three novel 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazoles were designed,synthesized and characterized by IR,NMR and APCI-MS.3-o-Fluorophenyl-6-(4-decarboxydehydroabietyl)-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazole(6a,C28H31FN4S) was structurally determined by single-crystal X-ray diffraction.The crystal belongs to the orthorhombic system,space group P212121 with a=6.0153(14),b=12.2577(19),c=34.055(3),V=2511.0(7)3,Z=4,Mr=474.63,Dc=1.255Mg/m3,λ=0.71073 ,μ(MoKα)=0.160 mm-1,F(000)=1008,the final R=0.0555 and wR=0.1248 for 3094 observed reflections with I2σ(I).There are six rings in the crystal structure of the title compound.The dihedral angle between 1,2,4-triazole and 1,3,4-thiadiaole rings is 1.4o,and that between 1,2,4-triazole and benzene ring D 25.5o.     

Synthesis and characterisation of thieno[3,2-b]thiophene-based linear shaped liquid crystals

A series of thieno[3,2-b]thiophene-based liquid crystalline molecules has been synthesised. To investigate the effects of alkyl substituent groups and structure of mesogenic cores, eight kinds of thieno[3,2-b]thiophene-based molecules containing different alkyl substituent groups and mesogenic cores have been synthesised. These molecules were characterised by differential scanning calorimetry, polarising optical microscopy, ultraviolet–visible absorption spectroscopy, fluorescence spectroscopy, cyclic voltammetry and polarised fluorescence spectroscopy. The results indicated that the thieno[3,2-b]thiophene-based donor-acceptor-donor (D-A-D) type molecules showed the presence of a smectic A phase. Changes in the length of alkyl substituents and mesogenic cores affected the phase transitions, optical and electrochemical properties of the molecules.     

Synthesis and Crystal Structure of a Novel Calix [8] arene Ester Derivative

The synthesis and crystal structure of a novel calix[8] arene ester are reported herein. The calix [8] arene ester derivative has been characterized by IR,NMR and X-ray crystal analysis. The X-ray structure analysis revealed that the 8 phenolic hydroxy groups of the calix [8] arene have been substituted by 4 diethyl dibromomalonate molecules with each two adjacent hydroxy oxygen atoms attached to a bridge diethyl malonate.     

Synthesis of 2,10,11-Trisubstituted Indolo[3,2-b]quinolines

A new method has been developed for the synthesis of derivatives of indolo[3,2-b]quinolines-11 based on N-oxidization of 2-nitro-10-substituted indolo[3,2-b]quinolines with subsequent conversion of the mixtures obtained into 2-nitro-11-substituted indolo[3,2-b]quinolinones-11. A series of 2-nitro-11-substituted indolo[3,2-b]quinolines was prepared.     

Synthesis and Herbicidal Activity of 2-Benzoyliminopyrimido[3,2-b]-1 2,4-Thiadiazolines

SincethesynthesisandherbicidalactivityofDPX-4l89wasreportedinl98o,awidevarietyofsulfonylureaswithimprovedselectivityand/oreffectivenesshavebeendeveloped'-'.Inacontinuingstudyonthesynthesisandherbicidalactivityofthiophenesulfonylureaandsubstitutedbenzenesulfonylureaderivatives'-',wehavefoundthatsulfonylureaherbicideshaveexcellentherbicidalactivityagainstawiderangeofweeds,butmostofthemwerenotselectivelyactiveherbicides.Inthispaperwedescribethesynthesisandherbicidalactivityofthirteen3-benzoly-l-…     

海洋生物碱2,3-二羟基-10-溴吲哚[3,2-a]咔唑的简易合成

2,3-二羟基-10-溴吲哚[3,2-a]咔唑(1)是一种从海绵体中提取的具有多种潜在生物活性的天然海洋生物碱.本文作者以3,6-二溴吲哚(2)与5,6-二乙酰氧基吲哚(3)为原料,经过酸催化偶联、分子间成环两步关键反应构建吲哚[3,2-a]咔唑母核;所构建的吲哚[3,2-a]咔唑母核在碱性条件下水解脱去酚羟基上的酯基,即得到目标化合物1,总收率为48%.     

Synthesis and Structure of 2-Isobutyl-6-(2'''',4''''-dichlorophenyl)imidazo[2,1-b]-1,3,4-thiadiazole

1INTRODUCTIONThethiadiazoleandimidazolecompoundsareextensivelystudiedduetotheirspectrumbioacti-vities[1～4].Amongthem,theimidazo[2,1-b]-1,3,4-thiadiazolederivativesarepharmaceuticallyimpor-tantbecauseoftheirimmunostimulant[5],antifugal[6],antimicrobial[7]…     

Synthesis and Antioxidant,Anti-Inflammatory,and Analgesic Activity of Novel Polycyclic Pyrimido[4,5-b]quinolines

The behavior of the 2-methylthio-pyrimido[4,5-b]quinolin-4-one towards differently substituted amines is reported. Also, the reactivity of 3-aminothiazolo[3′,2′ :1,2]-pyrimido[4,5-b]quinoline-2-carbonitrile towards formic acid, urea, thiourea, formamide, and carbon disulfide is discussed. Some of the synthesized derivatives possess biological activities as anti-inflammatory and analgesic agents. Some of these selective biologically active compounds were screened for antioxidant properties.     

A concise synthesis of functionalized 2,3-dihydrofuro[3,2-b], [3,2-c], and [2,3-b]pyridines

A strategy for the efficient and rapid one-pot synthesis of 2-aryl-2,3-dihydrofuro[3,2-b], [3,2-c], and [2,3-b]pyridines from readily available o-nitropicolines and aromatic aldehydes is described. The key transformation involves reaction of o-nitropicolines with aromatic aldehydes in the presence of TBAF and Hünig's base giving rise to functionalized products having molecular complexity suitable for further manipulation.     

An Efficient Method for the Synthesis of Indolo[3,2-c]quinoline Derivatives Catalyzed by Iodine

The reaction of Schiff base and indole catalyzed by iodine in DMA, subsequently treated with DDQ, gave indolo[3,2‐c]quinoline derivatives in good yields. The structure of 3e was confirmed by X‐ray diffraction analysis.