• <tr id="yyy80"></tr>
  • <sup id="yyy80"></sup>
  • <tfoot id="yyy80"><noscript id="yyy80"></noscript></tfoot>
  • 99热精品在线国产_美女午夜性视频免费_国产精品国产高清国产av_av欧美777_自拍偷自拍亚洲精品老妇_亚洲熟女精品中文字幕_www日本黄色视频网_国产精品野战在线观看 ?

    The Synthesis of the Thiazolyl-Pyrazoline Derivatives with 1,2,3-Triazole Moiety

    2012-11-14 08:47:49CHENFeiLIUFangmingCHENSenlinDONGZhiqiang
    關(guān)鍵詞:氫譜化工學院噻唑

    CHEN Fei, LIU Fang-ming, CHEN Sen-lin, DONG Zhi-qiang

    (College of Materials and Chemical Engineering, Hangzhou Normal University, Hangzhou 310036, China)

    The Synthesis of the Thiazolyl-Pyrazoline Derivatives with 1,2,3-Triazole Moiety

    CHEN Fei, LIU Fang-ming, CHEN Sen-lin, DONG Zhi-qiang

    (College of Materials and Chemical Engineering, Hangzhou Normal University, Hangzhou 310036, China)

    Novel pyrazoline derivatives with 1,2,3-triazole and thiazole moiety were synthesized by the cyclization of 3,5-diphenyl-1-thiocarbamoylpytazolines(1), and 2-bromo-1-(2-phenyl-1,2,3-triazol-4-yl) ethanone (2) in ethanol. The structure of these compounds was confirmed with IR,1H NMR, mass spectral and elemental analysis.

    1,2,3-triazoles; pyrazoline; thiazole

    0 Introduction

    In recent years, interest in the nitrogen- and sulfur-containing heterocyclic compounds significatively increased mainly due to their versatile agricultural and biological activities. Pyrazoline derivatives have been proven to show a broad spectrum of biological activities including fungicidal, insecticidal, antiproliferative and Cannabinoid receptor antagonists[1-4]. In addition, the 1,2,3-triazole motif makes up the core structure of some compounds with pharmaceutical activities such as anti-influenza, antibacterial, treating cryptosporidiosis and Gaucher disease[5-8]. Furthermore, the thiazole moiety is present in a number of drugs as a pharmacophore, and there are numerous examples of biological activities in the literature including antimicrobial, insecticidal, antibacterial and antiviral activity[9-12].

    In our previous papers[13-14], we reported a series of novel pyrazoline derivatives with both thiazole and 1,2,3-triazole in the molecule with a view to obtain higher bioactivity leading compounds. In this publication, we tried to replace the 1-aryl-2-bromoethanones with 2-bromo-1-(2-phenyl-1,2,3-triazol-4-yl) ethanone and synthesized some new thiazolyl-pyrazoline derivatives bearing 1,2,3-triazole moiety, 2-(3,5-diaryl-4,5-dihydro-1H-pyrazol-1-yl)-4-[2H-(2-phenyl-1,2,3-triazol)-4-yl] thiazoles . The synthetic route is shown in Scheme 1.

    Scheme 1 The synthesis route of title compounds

    1 Experimental

    1.1 Materials and synthesis

    All the solvents and materials were of reagent grade and purified as required. Reactions were monitored by TLC. Melting points were determined by use of a Mettler FP-5 melting point apparatus and are uncorrected. IR spectra were recorded as KBr pellets on a Bruker Equinox 55 FT-IR spectrophotometer.1H NMR spectra were recorded on a Bruker 400 MHz spectrometer using TMS as internal reference and CDCl3as solvent. Mass spectra were acquired with an Agilent 5975 Instrument (EI, 70 eV).

    1.2 The synthesis of 3,5-diphenyl-1-thiocarbamoylpyrazoline (1)

    Corresponding chalcone[15](7 mmol) and thiosemicarbazide (0.764 g, 8.4 mmol) was refluxed in ethanol (40 mL). After dissolution of the reactants, a solution of KOH (12.5 mmol) in water (5 mL) was added dropwise. The solution was refluxed for a further 4 h. The reaction mixture was allowed to cool, poured into crushed ice, and the solid mass separated out was filtered, washed with cold ethanol, dried, and crystallized from ethanol/water.

    1.3 The synthesis of 2-(3,5-diaryl-4,5-dihydro-1H-pyrazol-1-yl)-4-[2H-(2-phenyl-1,2,3-triazol)-4-yl] thiazoles (3a-3l)

    A mixture of 2-bromo-1-(2-phenyl-1,2,3-triazol-4-yl) ethanones 2 (1 mmol) and equivalent amounts of 3,5-diphenyl-1-thiocarbamoylpyrazoline1was refluxed in anhydrous ethanol (20 mL). After completion of the reaction (monitored by TLC), the mixture was allowed to cool. Then the solid product was collected. The product was recrystallized from DMF/ethanol.

    3a: Yield 82%, m.p. : 191~192 °C. Yellow solid, IR, ν/cm-l: 2808, 2715 (CH2, CH), 1632, 1596, 1495 (C=N, C=C), 760 (C—S—C);1H NMR (CDCl3, 400 MHz)δ: 7.88 (s, 1H, 1,2,3-triazole-H), 8.08~6.98 (m, 15H, Ar-H), 7.15(s, 1H, thiazole-H), 5.71 (dd, 1H, Hx, Jax= 6.4Hz, Jbx= 11.9Hz), 3.93 (dd, 1H, Hb, Jbx= 11.9Hz, Jab= 17.2Hz), 3.33 (dd, 1H, Ha, Jax= 6.4Hz, Jab= 17.2Hz); MS (EI) m/z (%): 448 (M+), 344, 242, 103, 91, 77; Analyses (%), C26H20N6S: C, 69.62; H, 4.49; N, 18.74; S, 7.15; Found: C, 69.64; H, 4.48; N, 18.75; S, 7.15.

    3b: Yield 86%, m.p. : 165~166 °C. Yellow solid, IR, ν/cm-l: 2856, 2808, 2713 (CH3, CH2, CH), 1631, 1596, 1496 (C=N, C=C), 756 (C—S—C);1H NMR (CDCl3, 400 MHz)δ: 7.88 (s, 1H, 1,2,3-triazole-H), 8.08~6.88 (m, 14H, Ar-H), 7.16 (s, 1H, thiazole-H), 5.71 (dd, 1H, Hx, Jax= 6.4Hz, Jbx= 11.7Hz), 3.95 (dd, 1H, Hb, Jbx= 11.7Hz, Jab= 17.4Hz), 3.34 (dd, 1H, Ha, Jax= 6.4Hz, Jab= 17.4Hz); MS (EI) m/z (%): 482 (M+), 374, 242, 138, 103, 91, 77; Analyses (%), C26H19ClN6S: C, 64.66; H, 3.97; Cl, 7.34; N, 17.40; S, 6.63; Found: C, 64.65; H, 3.97; Cl, 7.35; N, 17.42; S, 6.62.

    3c: Yield 81%, m.p. : 158~159 °C. Yellow solid, IR, ν/cm-l: 2808, 2712 (CH2, CH), 1632, 1596, 1498 (C=N, C=C), 756 (C—S—C);1H NMR (CDCl3, 400 MHz)δ: 7.93 (s, 1H, 1,2,3-triazole-H), 8.09~6.94 (m, 14H, Ar-H), 7.13 (s, 1H, thiazole-H), 5.66 (dd, 1H, Hx, Jax= 6.2Hz, Jbx= 11.9Hz), 3.88 (dd, 1H, Ha, Jax= 6.2Hz, Jab= 17.2Hz), 3.32 (dd, 1H, Hb, Jbx= 11.9Hz, Jab= 17.2Hz), 2.34 (s, 1H, CH3); MS (EI) m/z (%): 462 (M+), 358, 242, 117, 103, 91, 77; Analyses (%), C27H22N6S: C, 70.11; H, 4.79; N, 18.17; S, 6.93; Found: C, 70.10; H, 4.78; N, 18.19; S, 6.93.

    3d: Yield 82%, m.p. : 116~117 °C. Yellow solid, IR, ν/cm-l: 2808, 2717 (CH2, CH), 1632, 1596, 1494 (C=N, C=C), 758 (C—S—C);1H NMR (CDCl3, 400 MHz)δ: 7.93 (s, 1H, 1,2,3-triazole-H), 8.09~6.90 (m, 14H, Ar-H), 7.12 (s, 1H, thiazole-H), 5.67 (dd, 1H, Hx, Jax= 6.4Hz, Jbx= 11.8Hz), 3.88 (dd, 1H, Ha, Jax= 6.4Hz, Jab= 17.3Hz), 3.33 (dd, 1H, Hb, Jbx= 11.8Hz, Jab= 17.3Hz), 3.85 (s, 1H, OCH3); MS (EI) m/z (%): 478 (M+), 374, 242, 134, 119, 103, 91, 77; Analyses (%), C27H22N6OS: C, 67.76; H, 4.63; N, 17.56; O, 3.35; S, 6.70; Found: C, 67.78; H, 4.64; N, 17.54; O, 3.33; S, 6.71.

    3e: Yield 83%, m.p. : 192~193 °C. Yellow solid, IR, ν/cm-l: 2802, 2713 (CH2, CH), 1631, 1597, 1495 (C=N, C=C), 757 (C—S—C);1H NMR (CDCl3, 400 MHz)δ: 7.97 (s, 1H, 1,2,3-triazole-H), 8.08~7.28 (m, 14H, Ar-H), 7.15(s, 1H, thiazole-H), 5.86 (dd, 1H, Hx, Jax= 5.8Hz, Jbx= 11.6Hz), 3.92 (dd, 1H, Ha, Jax= 5.8Hz, Jab= 17.6Hz), 3.34 (dd, 1H, Hb, Jbx= 11.6Hz, Jab= 17.5Hz); MS (EI) m/z (%): 482 (M+), 344, 242, 137, 103, 91, 77; Analyses (%), C26H19ClN6S: C, 64.66; H, 3.97; Cl, 7.33; N, 17.40; S, 6.64; Found: C, 64.67; H, 3.97; Cl, 7.36; N, 17.39; S, 6.61.

    3f: Yield 81%, m.p. : 187~188 °C. Yellow solid, IR, ν/cm-l: 1632, 1596, 1493 (C=N, C=C), 752 (C—S—C);1H NMR (CDCl3, 400 MHz)δ: 7.90 (s, 1H, 1,2,3-triazole-H), 8.06~7.32 (m, 13H, Ar-H), 7.16 (s, 1H, thiazole-H), 5.73 (dd, 1H, Hx, Jax= 6.2Hz, Jbx= 12.0Hz), 3.90 (dd, 1H, Ha, Jax= 6.2Hz, Jab= 17.4Hz), 3.29 (dd, 1H, Hb, Jbx= 12.0Hz, Jab= 17.4Hz); MS (EI) m/z (%): 516 (M+), 378, 242, 138, 103, 91, 77; Analyses (%), C26H18Cl2N6S: C, 60.35; H, 3.51; Cl, 13.70; N, 16.24; S, 6.20; Found: C, 60.36; H, 3.52; Cl, 13.70; N, 16.22; S, 6.20.

    3g: Yield 80%, m.p. : 274~275 °C. Yellow solid, IR, ν/cm-l: 1631, 1595, 1493 (C=N, C=C), 751 (C—S—C);1H NMR (CDCl3, 400 MHz)δ: 7.90 (s, 1H, 1,2,3-triazole-H), 8.06~6.92 (m, 13H, Ar-H), 7.15 (s, 1H, thiazole-H), 5.72 (dd, 1H, Hx, Jax= 6.2Hz, Jbx= 12.0Hz), 3.91 (dd, 1H, Ha, Jax= 6.2Hz, Jab= 17.2Hz), 3.32 (dd, 1H, Hb, Jbx= 12.0Hz, Jab= 17.2Hz), 2.33 (s, 1H, CH3); MS (EI) m/z (%): 496 (M+), 358, 242, 117, 91, 77; Analyses (%), C27H21ClN6S: C, 65.25; H, 4.26; Cl, 7.13; N, 16.91; S, 6.45; Found: C, 65.25; H, 4.24; Cl, 7.12; N, 16.93; S, 6.46.

    3h: Yield 82%, m.p. : 163~164 °C. Yellow solid, IR, ν/cm-l: 2805, 2716 (CH2, CH), 1632, 1596, 1493 (C=N, C=C), 757 (C—S—C);1H NMR (CDCl3, 400 MHz)δ: 7.90 (s, 1H, 1,2,3-triazole-H), 8.06~6.90 (m, 13H, Ar-H), 7.16 (s, 1H, thiazole-H), 5.71 (dd, 1H, Hx, Jax= 6.2Hz, Jbx= 11.8Hz), 3.91 (dd, 1H, Ha, Jax= 6.2Hz, Jab= 17.3Hz), 3.32 (dd, 1H, Hb, Jbx= 11.8Hz, Jab= 17.3Hz), 3.85 (s, 1H, OCH3); MS (EI) m/z (%): 512 (M+), ; Analyses (%), C27H21ClN6OS: C, 63.21; H, 4.13; Cl, 6.91; N, 16.38; O, 3.12; S, 6.25; Found: C, 63.19; H, 4.14; Cl, 6.92; N, 16.36; O, 3.12; S, 6.27.

    3i: Yield 78%, m.p. : 192~193 °C. Yellow solid, IR, ν/cm-l: 2808, 2718 (CH2, CH), 1632, 1592, 1516 (C=N, C=C), 758 (C—S—C);1H NMR (CDCl3, 400 MHz)δ: 7.92 (s, 1H, 1,2,3-triazole-H), 8.02~6.94 (m, 13H, Ar-H), 7.12 (s, 1H, thiazole-H), 5.67 (dd, 1H, Hx, Jax= 6.5Hz, Jbx= 11.8Hz), 3.88 (dd, 1H, Ha, Jax= 6.5Hz, Jab= 17.6Hz), 3.32 (dd, 1H, Hb, Jbx= 11.8Hz, Jab= 17.6Hz), 3.87 (s, 1H, OCH3); MS (EI) m/z (%): 478 (M+), 344, 242, 133, 103, 91, 77; Analyses (%), C27H22N6OS: C, 67.76; H, 4.64; N, 17.56; O, 3.34; S, 6.70; Found: C, 67.75; H, 4.63; N, 17.57; O, 3.33; S, 6.70.

    3j: Yield 82%, m.p. : 165~166 °C. Yellow solid, IR, ν/cm-l: 2808, 2713 (CH2, CH), 1631, 1592, 1514 (C=N, C=C), 758 (C—S—C);1H NMR (CDCl3, 400 MHz)δ: 7.92 (s, 1H, 1,2,3-triazole-H), 8.02~6.94 (m, 13H, Ar-H), 7.12 (s, 1H, thiazole-H), 5.65 (dd, 1H, Hx, Jax= 6.2Hz, Jbx= 11.8Hz), 3.91 (dd, 1H, Ha, Jax= 6.2Hz, Jab= 17.2Hz), 3.32 (dd, 1H, Hb, Jbx= 11.8Hz, Jab= 17.2Hz), 3.87 (s, 1H, OCH3); MS (EI) m/z (%): 512 (M+), 374, 242, 134, 119, 103, 91, 77; Analyses (%), C27H21ClN6OS: C, 63.21; H, 4.13; Cl, 6.91; N, 16.38; O, 3.12; S, 6.25; Found: C, 63.22; H, 4.13; Cl, 6.91; N, 16.37; O, 3.10; S, 6.27.

    3k: Yield 82%, m.p. : 153~154 °C. Yellow solid, IR, ν/cm-l: 2864, 2806, 2719 (CH3,CH2, CH), 1631, 1592, 1513 (C=N, C=C), 752 (C—S—C);1H NMR (CDCl3, 400 MHz)δ: 7.93 (s, 1H, 1,2,3-triazole-H), 8.09~6.94 (m, 13H, Ar-H), 7.12 (s, 1H, thiazole-H), 5.67 (dd, 1H, Hx, Jax= 6.4Hz, Jbx= 11.8Hz), 3.88 (dd, 1H, Ha, Jax= 6.4Hz, Jab= 17.3Hz), 3.32 (dd, 1H, Hb, Jbx= 11.8Hz, Jab= 17.3Hz), 3.86 (s, 1H, OCH3), 2.32 (s, 1H, CH3); MS (EI) m/z (%): 492 (M+), 358, 242, 133, 117, 91, 77; Analyses (%), C28H24N6OS: C, 68.27; H, 4.91; N, 17.06; O, 3.25; S, 6.51; Found: C, 68.29; H, 4.94; N, 17.03; O, 3.25; S, 6.49.

    3l: Yield 82%, m.p. : 181~182 °C. Yellow solid, IR, ν/cm-l: 2807, 2715 (CH2, CH), 1632, 1592, 1514 (C=N, C=C), 757 (C—S—C);1H NMR (CDCl3, 400 MHz)δ: 7.93 (s, 1H, 1,2,3-triazole-H), 8.09~6.87 (m, 13H, Ar-H), 7.13 (s, 1H, thiazole-H), 5.67 (dd, 1H, Hx, Jax= 6.2Hz, Jbx= 12.0Hz), 3.89 (dd, 1H, Ha, Jax= 6.2Hz, Jab= 17.4Hz), 3.33 (dd, 1H, Hb, Jbx= 12.0Hz, Jab= 17.4Hz), 3.86 (s, 1H, OCH3), 3.87 (s, 1H, OCH3); MS (EI) m/z (%): 508 (M+), 374, 242, 133, 103, 91, 77; Analyses (%), C27H22N6OS: C, 66.12; H, 4.76; N, 16.52; O, 6.29; S, 6.31; Found: C, 66.15; H, 4.76; N, 16.51; O, 6.27; S, 6.31.

    2 Results and discussion

    The starting compounds 1,3-diaryl-2-propenones which were readily obtained by the reaction of aromatic aldehydes and 1-arylethanones via the Claisen-Schmidt condensation reaction in good yield, subsequently reacted with thiosemicarbazide in the presence of sodium hydroxide in ethanol, to give 3,5-diphenyl-1-thiocarbamoylpyrazolines[16](1), then underwent condensation with 2-bromo-1-(2-phenyl-1,2,3-triazol-4-yl)ethanones (2)[17]in refluxing ethanol resulted in the formation of the desired cyclized title products (3a-l) in 78~86%.

    The IR spectral, mass spectra, and1H NMR spectral data gave strong evidence for the structures of 3a-l.1H NMR revealed two singlets at 7.97~7.88, and 7.16~7.12 ppm which could be attributed to the pyrazole-H and 1,2,3-triazole-H, respectively. The presence of a multiplet at 8.09~6.87 ppm was ascribed to the aromatic protons. Remarkably, three distinct double of doublets of the ABX system of the pyrazoline ring (Jab= 17.2-17.6, Jax= 5.8-6.5, Jbx= 12.0-11.6 Hz) were observed at δ 5.86-5.65, 3.95-3.88, 3.34-3.29 ppm, respectively. Their infrared spectra contained strong absorption bands for C=N double bonds at 1631-1632 cm-1. The EI mass spectra of compounds 3a-lrevealed the existence of the molecular ion peaks and anticipated fragmentation peaks, which were in good agreement with the given structures of products. For example, the mass spectrum of 3a(Fig. 1) had molecular ion peaks at m/z 448, 344 (M-C8H8), 242 (M-C15H12N1), 103 (M-C18H13N6S), 91 (C7H7), 77 (C6H5), consistent with the molecular formula.

    Fig. 1 Proposed fragmentation patterns of 3a

    [1] Zhao Peiliang, Wang fu, Zhang Mingzhi,etal. Synthesis, Fungicidal, and Insecticidal Activities of β-Methoxyacrylate-Containing N-Acetyl Pyrazoline Derivatives[J]. Agric Food Chem,2008,56(22):10767-10773.

    [2] Frank E, Mucsi Z, Zupkó I,etal. Efficient Approach to Androstene-Fused Arylpyrazolines as Potent Antiproliferative Agents. Experimental and Theoretica Studies of Substituent Effects on BF3-Catalyzed Intramolecular [3+2] Cycloadditions of Olefinic Phenylhydrazones[J]. J Am Chem Soc,2009,131(11):3894-3904.

    [3] Du Xiaohui, Guo Chun, Hansell E,etal. Synthesis and Structure -Activity Relationship Study of Potent Trypanocidal Thio Semicarbazone Inhibitors of the Trypanosomal Cysteine Protease Cruzain[J]. J Med Chem,2002,45(13):2695-2707.

    [4] Lange J H M, Coolen H A C, Stuivenberg H H,etal. Synthesis, Biological Properties, and Molecular Modeling Investigations of Novel 3,4-Diarylpyrazolines as Potent and Selective CB 1 Cannabinoid Receptor Antagonists[J]. J Med Chem,2004,47(3):627-643.

    [5] Cheng Huiming, Wan Junting, Lin Meng-i,etal. Design, Synthesis, and in Vitro Biological Evaluation of 1H-1,2,3-Triazole-4-carboxamide Derivatives as New Anti-influenza A Agents Targeting Virus Nucleoprotein[J]. J Med Chem,2012,55(5):2144-2153.

    [6] Genin M J, Allwine D A, Anderson D J,etal. Substituent Effects on the Antibacterial Activity of Nitrogen-Carbon-Linked (Azolylphenyl)oxazolidinones with Expanded Activity Against the Fastidious Gram-Negative Organisms Haemophilus Influenzae and Moraxella catarrhalis[J]. J Med Chem,2000,43(5):953-970.

    [7] Maurya S K, Gollapalli D R, Kirubakaran S,etal. Triazole Inhibitors of Cryptosporidium parvumInosine 5'-Monophosphate Dehydrogenase[J]. J Med Chem,2009,52(15):4623-4630.

    [8] Dìaz L, Bujons J, Casas J,etal. Click Chemistry Approach to New N-Substituted Aminocyclitols as Potential Pharmacological Chaperones for Gaucher Disease[J]. J Med Chem,2010,53(14):5248-5255.

    [9] Katsura Y, Tomishi T, Inoue Y,etal. Anti-Helicobacter pylori Agents. 4. 2-(Substituted guanidino)-4-phenylthiazoles and Some Structurally Rigid Derivatives[J]. J Med Chem,2000,43(17):3315-3321.

    [10] Yu Haibo, Qin Zhenfeng, Dai Hong,etal. Synthesis and Insecticidal Activity of N-Substituted (1,3-Thiazole)alkyl Sulfoximine Derivatives[J]. Agric Food Chem,2008,56(23):11356-11360.

    [11] Romagnoli R, Baraldi P G, Brancale A,etal. Convergent Synthesis and Biological Evaluation of 2-Amino-4-(3',4',5'-trimethoxyphenyl)-5-aryl Thiazoles as Microtubule Targeting Agents[J]. J Med Chem,2011,54(14):5144-5153.

    [12] Sharma S K, Tandon M, Lown J W. Design and Synthesis of Novel Thiazole-Containing Cross-Linked Polyamides Related to the Antiviral Antibiotic Distamycin[J]. Org Chem,2000,65(4):1102-1107.

    [13] Shi Hai, Liu Fangming, Shen Songwei. Synthesis and Spectral Characterization of Some Novel Thiazolyl-Pyrazoline Derivatives Containing 1,2,3-Triazole Moiety[J]. Phosphorus Sulfur and Silicon,2011,186(2):263-270.

    [14] Chen Shengqin, Zhang Yichao, Liu Fangming. Synthesis and Spectral Characterization of Some New Thiazolyl-Pyrazolines Bearing 1,2,4-Triazole Moiety[J]. Phosphorus Sulfur and Silicon,2011,186(2):319-325.

    [15] Gresser R, Hartmann H, Wrackmeyer M,etal. Synthesis of thiophene-substituted aza-BODIPYs and their optical and electroche mical properties[J]. Tetrahedron,2011,67:7148-7155.

    [16] Liu Xiangfeng, Shi Daohua. Research progress in the synthesis of chalcone[J]. Applied Chemical Industry,2009,38(8):1210-1219.

    [17] Wu Xiaolong, Ye Jiawei, Yang Debao,etal. Synthesis and characterization of 1,4-diaryl-3-(ethoxycarbonyl)-5-[2-phenyl-1,2,3-triazolyl)carbonyl]-4,5-dihydropyrazole derivatives[J].Chin J Org Chem,2010,30(10):1502-1507.

    新型含1,2,3-三唑基的噻唑-吡唑啉衍生物的合成

    陳 菲,劉方明,陳森林,董志強

    (杭州師范大學材料與化學化工學院,浙江 杭州 310036)

    1-氨基硫代甲酰基-3,5-二芳基-4,5-二氫吡唑(1)和1-(2-苯基-1,2,3-三唑-4-基)-2-溴乙酮(2)在乙醇中回流環(huán)化, 制備一系列新型含噻唑基、1,2,3-三唑基的吡唑啉衍生物, 其結(jié)構(gòu)經(jīng)紅外、核磁氫譜、質(zhì)譜和元素分析確認.

    1,2,3-三唑;吡唑啉;噻唑

    date:2012-03-16

    LIU Fang-ming(1966—),male, professor, engaged in synthesis of heterocyclic compound. E-mail: fmilu859@sohu.com

    11.3969/j.issn.1674-232X.2012.05.008

    O626.25ArticlecharacterA

    1674-232X(2012)05-0420-06

    猜你喜歡
    氫譜化工學院噻唑
    使固態(tài)化學反應100%完成的方法
    波譜分析教學中核磁共振氫譜解析的教學設計*
    云南化工(2023年7期)2023-08-01 07:59:34
    阿爾茨海默病血清代謝物的核磁共振氫譜技術(shù)分析
    Study on related substances in ceftizoxime sodium
    基于苯并噻唑用作分析物檢測的小分子熒光探針
    云南化工(2021年7期)2021-12-21 07:27:22
    國家開放大學石油和化工學院學習中心列表
    【鏈接】國家開放大學石油和化工學院學習中心(第四批)名單
    核磁共振氫譜在阿司匹林合成實驗中的應用
    《化工學報》贊助單位
    化工學報(2016年3期)2016-03-14 08:37:00
    高效液相色譜法同時測定反應液中的苯并噻唑和2-巰基苯并噻唑
    全区人妻精品视频| 在线观看免费日韩欧美大片 | 国产精品一区www在线观看| 国产成人精品婷婷| 高清黄色对白视频在线免费看| 人妻一区二区av| tube8黄色片| 免费黄色在线免费观看| 久久综合国产亚洲精品| 国产一区二区三区av在线| 亚洲,欧美,日韩| 久久精品国产a三级三级三级| 一区二区三区免费毛片| 精品国产乱码久久久久久小说| 成人午夜精彩视频在线观看| 99热这里只有精品一区| 99久国产av精品国产电影| 91久久精品国产一区二区成人| 免费久久久久久久精品成人欧美视频 | 国产永久视频网站| 边亲边吃奶的免费视频| 国产毛片在线视频| 久久久久精品久久久久真实原创| 亚洲经典国产精华液单| 免费人成在线观看视频色| 乱码一卡2卡4卡精品| 国产亚洲最大av| 亚洲少妇的诱惑av| 欧美xxxx性猛交bbbb| 国产一区亚洲一区在线观看| 欧美精品人与动牲交sv欧美| 蜜桃在线观看..| 一级黄片播放器| 好男人视频免费观看在线| 国产免费视频播放在线视频| 久久热精品热| 国产成人午夜福利电影在线观看| 丁香六月天网| a级毛色黄片| 亚洲精品成人av观看孕妇| 亚洲av福利一区| 日韩中字成人| 国产 一区精品| 国产伦理片在线播放av一区| 亚洲人成网站在线播| 欧美 亚洲 国产 日韩一| 少妇的逼好多水| 国产精品一国产av| 大话2 男鬼变身卡| 人妻制服诱惑在线中文字幕| 午夜免费男女啪啪视频观看| 精品一区二区三卡| 欧美成人精品欧美一级黄| 91精品国产国语对白视频| 国产男人的电影天堂91| 国产成人91sexporn| 国产精品.久久久| 久久av网站| 成人综合一区亚洲| videos熟女内射| 99热这里只有精品一区| 亚洲高清免费不卡视频| 午夜福利视频精品| 国精品久久久久久国模美| 色哟哟·www| 久久久久久久久大av| 桃花免费在线播放| 哪个播放器可以免费观看大片| 亚洲经典国产精华液单| 欧美+日韩+精品| 中文字幕人妻熟人妻熟丝袜美| 大香蕉97超碰在线| 2021少妇久久久久久久久久久| 91久久精品国产一区二区成人| 亚洲综合色网址| 欧美另类一区| 国产高清国产精品国产三级| 亚洲美女视频黄频| av免费观看日本| 18在线观看网站| 人人妻人人爽人人添夜夜欢视频| 中文字幕人妻熟人妻熟丝袜美| 内地一区二区视频在线| 国产深夜福利视频在线观看| 99久久精品一区二区三区| 看十八女毛片水多多多| 80岁老熟妇乱子伦牲交| 狠狠精品人妻久久久久久综合| 老司机影院成人| 97在线视频观看| 99久久中文字幕三级久久日本| 亚洲熟女精品中文字幕| 精品一区二区免费观看| a级毛片在线看网站| av.在线天堂| 国产男女超爽视频在线观看| 亚洲精华国产精华液的使用体验| 国产免费又黄又爽又色| 亚洲av在线观看美女高潮| 国产精品蜜桃在线观看| 久热久热在线精品观看| 精品少妇内射三级| 亚洲欧美成人综合另类久久久| 亚洲熟女精品中文字幕| 制服诱惑二区| 久久久久久久久久人人人人人人| 久久久欧美国产精品| 亚洲三级黄色毛片| 精品亚洲成a人片在线观看| 久久久国产欧美日韩av| 一边摸一边做爽爽视频免费| 久久综合国产亚洲精品| 国产精品三级大全| 国产成人精品婷婷| 九色成人免费人妻av| 国产精品女同一区二区软件| av在线播放精品| 国产亚洲最大av| 激情五月婷婷亚洲| av天堂久久9| 成人18禁高潮啪啪吃奶动态图 | 亚洲精品乱码久久久久久按摩| 91午夜精品亚洲一区二区三区| 国产精品偷伦视频观看了| 成人黄色视频免费在线看| 亚洲精品日韩在线中文字幕| 亚洲精品aⅴ在线观看| 天堂中文最新版在线下载| 91国产中文字幕| 国产一区二区在线观看av| av免费观看日本| 人人妻人人澡人人看| www.色视频.com| 精品久久蜜臀av无| 精品久久国产蜜桃| 夫妻午夜视频| 成人18禁高潮啪啪吃奶动态图 | 国产精品久久久久久av不卡| 观看av在线不卡| 欧美激情 高清一区二区三区| 久久久a久久爽久久v久久| 国产精品一二三区在线看| 最近最新中文字幕免费大全7| 人成视频在线观看免费观看| 国产成人午夜福利电影在线观看| 国产亚洲精品第一综合不卡 | 18禁在线无遮挡免费观看视频| 美女国产视频在线观看| av免费观看日本| 午夜视频国产福利| 日韩一区二区三区影片| 美女福利国产在线| 免费大片18禁| 夫妻午夜视频| 少妇的逼好多水| 日本wwww免费看| 久久免费观看电影| 女人久久www免费人成看片| 在线观看免费视频网站a站| 亚洲三级黄色毛片| 国产日韩欧美在线精品| 久久久a久久爽久久v久久| 如何舔出高潮| 国产视频内射| 国产精品国产三级国产专区5o| 日本欧美国产在线视频| 欧美日韩视频高清一区二区三区二| 在线观看三级黄色| 亚洲色图 男人天堂 中文字幕 | 91在线精品国自产拍蜜月| 少妇人妻久久综合中文| 欧美日韩一区二区视频在线观看视频在线| 高清在线视频一区二区三区| 国产精品久久久久久精品古装| 久久久久国产精品人妻一区二区| 精品久久久久久久久亚洲| 精品国产一区二区三区久久久樱花| 人人妻人人爽人人添夜夜欢视频| 啦啦啦啦在线视频资源| 亚洲欧美清纯卡通| 制服人妻中文乱码| 国产亚洲最大av| 丰满乱子伦码专区| 久久ye,这里只有精品| 制服人妻中文乱码| 91久久精品国产一区二区三区| 国产亚洲最大av| 国产伦精品一区二区三区视频9| 久久精品国产自在天天线| 亚洲精品久久久久久婷婷小说| 午夜福利网站1000一区二区三区| 肉色欧美久久久久久久蜜桃| 色94色欧美一区二区| 久久婷婷青草| 伊人久久精品亚洲午夜| 午夜免费观看性视频| 人妻一区二区av| 精品酒店卫生间| 精品久久久噜噜| 夜夜爽夜夜爽视频| 免费人成在线观看视频色| 亚洲不卡免费看| 成人二区视频| 黄色视频在线播放观看不卡| 成人漫画全彩无遮挡| 精品少妇久久久久久888优播| 色视频在线一区二区三区| 人人澡人人妻人| 男男h啪啪无遮挡| av国产久精品久网站免费入址| 免费大片18禁| 啦啦啦视频在线资源免费观看| 视频中文字幕在线观看| 成人影院久久| 国产男人的电影天堂91| 日韩av免费高清视频| 18禁裸乳无遮挡动漫免费视频| 亚洲av.av天堂| 国产男人的电影天堂91| 亚州av有码| √禁漫天堂资源中文www| 国产成人av激情在线播放 | 国产黄色免费在线视频| 免费观看av网站的网址| 全区人妻精品视频| 国产有黄有色有爽视频| 如日韩欧美国产精品一区二区三区 | 色视频在线一区二区三区| 18禁在线播放成人免费| 欧美国产精品一级二级三级| 看非洲黑人一级黄片| 国产午夜精品久久久久久一区二区三区| 街头女战士在线观看网站| 国产精品无大码| 人人妻人人澡人人看| 欧美日韩精品成人综合77777| 一区在线观看完整版| 亚洲熟女精品中文字幕| 成人国产麻豆网| 亚洲精品色激情综合| av天堂久久9| 久久综合国产亚洲精品| 亚洲精品国产av成人精品| 亚洲av免费高清在线观看| 欧美精品亚洲一区二区| 日韩 亚洲 欧美在线| a 毛片基地| 欧美日韩亚洲高清精品| 男人爽女人下面视频在线观看| av国产精品久久久久影院| 亚洲成人手机| 日韩强制内射视频| 久久 成人 亚洲| 亚洲av免费高清在线观看| 黄色视频在线播放观看不卡| 日韩欧美精品免费久久| 亚洲国产色片| 韩国高清视频一区二区三区| 热re99久久精品国产66热6| 香蕉精品网在线| 亚洲精品乱码久久久v下载方式| 久热久热在线精品观看| 亚洲不卡免费看| 青春草视频在线免费观看| 国产伦理片在线播放av一区| 在线精品无人区一区二区三| 精品酒店卫生间| 寂寞人妻少妇视频99o| 18在线观看网站| 观看av在线不卡| 在线观看三级黄色| av天堂久久9| 国产免费视频播放在线视频| 最近2019中文字幕mv第一页| 在线观看www视频免费| 天堂俺去俺来也www色官网| 老熟女久久久| 中文字幕免费在线视频6| 国产乱来视频区| 国产精品久久久久久精品古装| 久热久热在线精品观看| 久久精品国产鲁丝片午夜精品| 一个人免费看片子| 久久久a久久爽久久v久久| 久久精品国产鲁丝片午夜精品| 97精品久久久久久久久久精品| 成人二区视频| 精品亚洲成国产av| 亚洲欧美色中文字幕在线| 亚洲精品乱码久久久v下载方式| 女的被弄到高潮叫床怎么办| 中文字幕人妻熟人妻熟丝袜美| 亚洲欧美成人精品一区二区| 制服诱惑二区| 中国三级夫妇交换| 亚州av有码| 最黄视频免费看| 国产极品粉嫩免费观看在线 | 午夜福利在线观看免费完整高清在| 满18在线观看网站| 国产精品偷伦视频观看了| 亚洲伊人久久精品综合| 亚洲精品乱久久久久久| 国产片内射在线| 在线观看免费高清a一片| 夜夜骑夜夜射夜夜干| 热re99久久精品国产66热6| 精品亚洲成a人片在线观看| 国产在线一区二区三区精| 国产精品不卡视频一区二区| 两个人的视频大全免费| 午夜av观看不卡| 制服诱惑二区| 日韩av免费高清视频| 国产片内射在线| 色视频在线一区二区三区| 插阴视频在线观看视频| 另类精品久久| 国产一级毛片在线| 午夜久久久在线观看| 丰满乱子伦码专区| 青春草亚洲视频在线观看| 午夜老司机福利剧场| 亚洲高清免费不卡视频| 国产精品嫩草影院av在线观看| 伊人久久国产一区二区| 国产亚洲精品第一综合不卡 | 日韩av不卡免费在线播放| 少妇被粗大猛烈的视频| 视频中文字幕在线观看| 人妻少妇偷人精品九色| 飞空精品影院首页| 欧美97在线视频| 国产淫语在线视频| 久久鲁丝午夜福利片| 我的老师免费观看完整版| 日本午夜av视频| 一级片'在线观看视频| 国产成人精品婷婷| 搡老乐熟女国产| 亚洲高清免费不卡视频| 晚上一个人看的免费电影| 欧美一级a爱片免费观看看| 欧美激情国产日韩精品一区| 满18在线观看网站| 成人毛片60女人毛片免费| 18在线观看网站| 日韩三级伦理在线观看| 欧美少妇被猛烈插入视频| 成人18禁高潮啪啪吃奶动态图 | 亚洲伊人久久精品综合| 97超视频在线观看视频| 3wmmmm亚洲av在线观看| 国产成人91sexporn| 男女国产视频网站| a级毛片免费高清观看在线播放| 亚洲成人手机| 久久99热6这里只有精品| 丝袜喷水一区| 国产成人freesex在线| 人成视频在线观看免费观看| 极品人妻少妇av视频| 2018国产大陆天天弄谢| 自拍欧美九色日韩亚洲蝌蚪91| 亚洲av福利一区| 大码成人一级视频| 99热网站在线观看| 亚洲国产精品一区三区| 国产黄片视频在线免费观看| 国精品久久久久久国模美| 九色亚洲精品在线播放| 亚洲精品国产av蜜桃| 久久这里有精品视频免费| 精品酒店卫生间| 伊人亚洲综合成人网| 亚洲国产av影院在线观看| 大码成人一级视频| 欧美日韩视频高清一区二区三区二| 久久ye,这里只有精品| 欧美日韩视频高清一区二区三区二| 国产综合精华液| 午夜91福利影院| 女性被躁到高潮视频| 中文字幕免费在线视频6| 午夜影院在线不卡| 伊人久久精品亚洲午夜| 纵有疾风起免费观看全集完整版| 欧美bdsm另类| 久久午夜综合久久蜜桃| 最近手机中文字幕大全| 亚洲国产精品国产精品| 看免费成人av毛片| 2022亚洲国产成人精品| 国产片内射在线| 国产精品熟女久久久久浪| 黑人巨大精品欧美一区二区蜜桃 | 国产免费一区二区三区四区乱码| 在线亚洲精品国产二区图片欧美 | 18在线观看网站| 色吧在线观看| 久久97久久精品| 伊人久久国产一区二区| 日韩在线高清观看一区二区三区| 交换朋友夫妻互换小说| 国产成人91sexporn| av国产久精品久网站免费入址| 啦啦啦啦在线视频资源| 成年女人在线观看亚洲视频| 黑丝袜美女国产一区| 欧美日韩精品成人综合77777| 久久精品久久精品一区二区三区| 99久久人妻综合| 久久亚洲国产成人精品v| 纵有疾风起免费观看全集完整版| 各种免费的搞黄视频| 人妻人人澡人人爽人人| 日本欧美视频一区| 99国产精品免费福利视频| 母亲3免费完整高清在线观看 | 国产成人freesex在线| 久久久午夜欧美精品| 亚洲国产欧美在线一区| 99九九在线精品视频| 中文字幕亚洲精品专区| 伦精品一区二区三区| 亚洲av国产av综合av卡| 亚洲精品色激情综合| 国产在视频线精品| 纯流量卡能插随身wifi吗| 亚洲第一av免费看| 亚洲国产精品一区二区三区在线| 菩萨蛮人人尽说江南好唐韦庄| 亚洲精品久久午夜乱码| 丝袜脚勾引网站| 麻豆精品久久久久久蜜桃| 热99久久久久精品小说推荐| 国产成人freesex在线| 亚洲精品自拍成人| 青春草亚洲视频在线观看| 日韩亚洲欧美综合| 97超碰精品成人国产| 婷婷色综合大香蕉| 91在线精品国自产拍蜜月| 亚洲av综合色区一区| 性高湖久久久久久久久免费观看| av福利片在线| 亚洲精品久久午夜乱码| 欧美成人精品欧美一级黄| 欧美+日韩+精品| 只有这里有精品99| 久久97久久精品| 精品亚洲乱码少妇综合久久| 校园人妻丝袜中文字幕| 欧美日韩国产mv在线观看视频| 亚洲美女搞黄在线观看| 亚洲精品美女久久av网站| 日韩伦理黄色片| 日日爽夜夜爽网站| 国产乱来视频区| a级片在线免费高清观看视频| av网站免费在线观看视频| 国产视频首页在线观看| 久久精品国产亚洲网站| 亚洲中文av在线| 中国三级夫妇交换| 亚洲国产精品成人久久小说| 日韩成人伦理影院| 黄片无遮挡物在线观看| 欧美性感艳星| 特大巨黑吊av在线直播| 国产免费福利视频在线观看| 一级毛片电影观看| 在线亚洲精品国产二区图片欧美 | 婷婷色麻豆天堂久久| 嫩草影院入口| 99久久精品一区二区三区| 国产午夜精品久久久久久一区二区三区| 久久午夜综合久久蜜桃| 狂野欧美白嫩少妇大欣赏| 久久精品国产亚洲av涩爱| 精品午夜福利在线看| 少妇 在线观看| 免费看不卡的av| 亚洲精品视频女| 精品一区在线观看国产| 少妇精品久久久久久久| 中文欧美无线码| 国产免费视频播放在线视频| 久久久久久久亚洲中文字幕| 亚洲av中文av极速乱| 天美传媒精品一区二区| 精品亚洲成a人片在线观看| freevideosex欧美| 日日摸夜夜添夜夜爱| 99久久人妻综合| 成人毛片60女人毛片免费| 国产综合精华液| h视频一区二区三区| 国产一区二区在线观看av| 婷婷成人精品国产| 国产在线免费精品| 18禁裸乳无遮挡动漫免费视频| a级毛色黄片| 精品国产露脸久久av麻豆| √禁漫天堂资源中文www| 亚洲av不卡在线观看| 高清视频免费观看一区二区| 26uuu在线亚洲综合色| 国产黄色视频一区二区在线观看| 伦理电影大哥的女人| 亚洲国产精品一区三区| 99久久人妻综合| 夫妻性生交免费视频一级片| 亚洲欧美日韩卡通动漫| 成年av动漫网址| 国产成人精品无人区| 久久午夜福利片| 欧美变态另类bdsm刘玥| 中文欧美无线码| 久久久精品区二区三区| 久久99精品国语久久久| 成人二区视频| 国产精品国产三级专区第一集| 美女国产高潮福利片在线看| 99精国产麻豆久久婷婷| 人妻人人澡人人爽人人| 插逼视频在线观看| 搡老乐熟女国产| 日韩一区二区视频免费看| 日韩三级伦理在线观看| 精品亚洲成a人片在线观看| 国产欧美日韩综合在线一区二区| 在线亚洲精品国产二区图片欧美 | 亚洲精品乱久久久久久| 在线免费观看不下载黄p国产| 免费高清在线观看日韩| 在线观看国产h片| av在线app专区| 国产黄频视频在线观看| 欧美 亚洲 国产 日韩一| 久久久精品免费免费高清| 欧美bdsm另类| 色婷婷久久久亚洲欧美| 伊人久久精品亚洲午夜| 免费久久久久久久精品成人欧美视频 | 一本大道久久a久久精品| 亚洲无线观看免费| 日韩三级伦理在线观看| 欧美xxxx性猛交bbbb| 国产探花极品一区二区| 久久人人爽人人爽人人片va| 乱人伦中国视频| 亚洲精品久久久久久婷婷小说| 精品国产国语对白av| 久久毛片免费看一区二区三区| 一区二区av电影网| 在线免费观看不下载黄p国产| 国产精品一区二区在线观看99| 日韩中文字幕视频在线看片| 亚洲精品中文字幕在线视频| 你懂的网址亚洲精品在线观看| 久久影院123| 蜜桃久久精品国产亚洲av| 亚洲精品aⅴ在线观看| 一二三四中文在线观看免费高清| 纯流量卡能插随身wifi吗| 日本黄大片高清| 人人妻人人添人人爽欧美一区卜| av在线app专区| 亚洲av国产av综合av卡| 国产成人a∨麻豆精品| 亚洲国产精品999| 日日撸夜夜添| 国产乱来视频区| 高清午夜精品一区二区三区| 综合色丁香网| 久久久久久人妻| 亚洲精品aⅴ在线观看| 观看美女的网站| 国产乱人偷精品视频| 亚洲精品视频女| 18禁在线无遮挡免费观看视频| 欧美变态另类bdsm刘玥| 美女国产视频在线观看| 午夜老司机福利剧场| 18+在线观看网站| av免费在线看不卡| 久久久精品区二区三区| 永久免费av网站大全| 91精品伊人久久大香线蕉| 黄色欧美视频在线观看| 日本午夜av视频| 在现免费观看毛片| 日本黄色日本黄色录像| 日韩av免费高清视频| 久久精品国产亚洲av天美| 亚洲欧美精品自产自拍| 日本av手机在线免费观看| 日日啪夜夜爽| 在线观看免费日韩欧美大片 | 曰老女人黄片| 伦理电影大哥的女人| 色哟哟·www| 精品亚洲成a人片在线观看| 久久精品久久久久久噜噜老黄| 国产精品国产三级国产专区5o| 欧美最新免费一区二区三区| 成人影院久久| 国产一区有黄有色的免费视频| 久久久久久久久大av| 亚洲精品国产av蜜桃| 免费高清在线观看视频在线观看| 国产精品久久久久久精品电影小说| 麻豆成人av视频| 国产男女内射视频|