Efficient Synthesis of Conjugated 1,3,4-Thiadiazole Hybrids through Palladium-Catalyzed Cross-Coupling of 2,5-Bis(4-bromophenyl)-1,3,4-thiadiazole with Boronic Acids

被引：10
作者：
Wroblowska, Monika [1 ]
Kudelko, Agnieszka [1 ]
Lapkowski, Mieczyslaw [2 ,3 ]
机构：
[1] Silesian Tech Univ, Dept Chem Organ Technol & Petrochem, PL-44100 Gliwice, Poland
[2] Silesian Tech Univ, Dept Phys Chem & Technol Polymers, PL-44100 Gliwice, Poland
[3] Polish Acad Sci, Ctr Polymer & Carbon Mat, PL-41819 Zabrze, Poland
来源：
SYNLETT | 2015年 / 26卷 / 15期
关键词：
heterocycles; cross-coupling; phase-transfer catalysis; palladium; catalysis; LIGHT-EMITTING-DIODES; ANTIMICROBIAL ACTIVITY; SIDE-CHAIN; DEVICE; ELECTROLUMINESCENCE; 1,3,4-OXADIAZOLES; ELECTROCHEMISTRY; DERIVATIVES; POLYMER;
D O I：
10.1055/s-0034-1378826
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
New derivatives of 2,5-bis(4-heteroarylphenyl)-1,3,4-thiadiazole were synthesized under Suzuki cross-coupling reactions from 2,5-bis(4-bromophenyl)-1,3,4-thiadiazole and commercially available boronic acids. Reactions were conducted in a two-phase solvent system in the presence of catalytic amounts of tetrakis(triphenylphosphine)palladium(0), cesium carbonate as a base, and tetrabutylammonium bromide playing a role of a phase-transfer catalyst.
引用
收藏
页码：2127 / 2130
页数：4
相关论文
共 50 条
  • [41] Synthesis and antimicrobial activities of some new biheterocyclic compounds containing 1,2,4-triazol-3-one and 1,3,4-thiadiazole moieties
    Bektas, Hakan
    Demirbas, Ahmet
    Demirbas, Neslihan
    Bayrak, Hacer
    Karaoglu, Senguel Alpay
    TURKISH JOURNAL OF CHEMISTRY, 2010, 34 (04) : 517 - 527
  • [42] Synthesis of Some New 1,3,4-Thiadiazole, Thiazole and Pyridine Derivatives Containing 1,2,3-Triazole Moiety
    Abdelriheem, Nadia A.
    Mohamed, Ali M. M.
    Abdelhamid, Abdou O.
    MOLECULES, 2017, 22 (02)
  • [43] SYNTHESIS AND ANTIMICROBIAL PROPERTIES OF NEW THIOSEMICARBAZIDE, 1,2,4-TRIAZOLE, AND 1,3,4-THIADIAZOLE DERIVATIVES OF SULFANYLACETIC ACID
    Popiolek, Lukasz
    Kosikowska, Urszula
    Dobosz, Maria
    Malm, Anna
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2012, 187 (04) : 468 - 481
  • [44] Efficient One-Pot Synthesis of 3,5-Disubstituted 1,3,4-Thiadiazole from Dithioesters under Mild Condition
    Kemparajegowda
    Swarup, Hassan A.
    Sandhya, Nagarakere C.
    Rangappa, Shobith
    Mantelingu, Kempegowda
    Rangappa, Kanchugarakoppal S.
    CHEMISTRYSELECT, 2019, 4 (15): : 4611 - 4614
  • [45] Hypolipidemic effect of novel 2,5-bis(4-hydroxybenzylidenamino)-1,3,4-thiadiazole as potential peroxisome proliferation-activated receptor-α agonist in acute hyperlipidemic rat model
    Hamadneh, Lama A.
    Sabbah, Dima A.
    Hikmat, Suhair J.
    Al-Samad, Luma A.
    Hasan, Mariam
    Al-Qirim, Tariq M.
    Hamadneh, Imad M.
    Al-Dujaili, Ammar H.
    MOLECULAR AND CELLULAR BIOCHEMISTRY, 2019, 458 (1-2) : 39 - 47
  • [46] Synergistic effect of iodide ions on inhibitive performance of 2,5-bis(4-methoxyphenyl)-1,3,4-thiadiazole during corrosion of mild steel in 0.5 M sulfuric acid solution
    Bentiss, Fouad
    Lebrini, Mounim
    Traisnel, Michel
    Lagrenee, Michel
    JOURNAL OF APPLIED ELECTROCHEMISTRY, 2009, 39 (08) : 1399 - 1407
  • [47] Synthesis and evaluation of benzosuberone embedded with 1,3,4-oxadiazole, 1,3,4-thiadiazole and 1,2,4-triazole moieties as new potential anti proliferative agents
    Yadagiri, Bandi
    Gurrala, Srikanth
    Bantu, Rajashaker
    Nagarapu, Lingaiah
    Polepalli, Sowjanya
    Srujana, Garimella
    Jain, Nishant
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2015, 25 (10) : 2220 - 2224
  • [48] Sebacoyl Isothiocyanate in the Synthesis of Bis (1,3,4-thiadiazole, 1,3,4-thiadiazolo[3,2-a]pyridine, 4-thiazolidinone, Chromenes, and Naphtho[1,2-b][1,4]oxazine) Derivatives
    Thabet, Hamdy Khamees
    ORIENTAL JOURNAL OF CHEMISTRY, 2020, 36 (02) : 320 - 326
  • [49] Regioselective Synthesis of 2-Amino-Substituted 1,3,4-Oxadiazole and 1,3,4-Thiadiazole Derivatives via Reagent-Based Cyclization of Thiosemicarbazide Intermediate
    Yang, Seung-Ju
    Lee, Seok-Hyeong
    Kwak, Hyun-Jung
    Gong, Young-Dae
    JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (02) : 438 - 444
  • [50] Synthesis of a Series of Novel 2-Amino-5-substituted 1,3,4-oxadiazole and 1,3,4-thiadiazole Derivatives as Potential Anticancer, Antifungal and Antibacterial Agents
    Em Canh Pham
    Tuyen Ngoc Truong
    Nguyen Hanh Dong
    Duy Duc Vo
    Tuoi Thi Hong Do
    MEDICINAL CHEMISTRY, 2022, 18 (05) : 558 - 573
12345