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 optical properties of new conjugated polymers composed of 1,3,4-thiadiazole and 2,5-dialkoxybenzene rings
    Sato, M
    Yamauchi, K
    Handa, M
    Kasuga, K
    MACROMOLECULAR RAPID COMMUNICATIONS, 2000, 21 (17) : 1234 - 1237
  • [42] catena-poly[[bis[triaqua[2,5-bis(4-pyridyl)-1,3,4-thiadiazole]cobalt(II)]]-μ4-tetravanadato]
    Zhang, XM
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2004, 60 : M1411 - M1413
  • [43] THE ORAL HYPOGLYCEMIC ACTIVITY OF 2,5-DIOXAMIDE DERIVATIVES OF 1,3,4-THIADIAZOLE
    OKE, JM
    OLOWOOKORUN, MO
    JAPANESE JOURNAL OF PHARMACOLOGY, 1989, 49 (01): : 135 - 138
  • [44] SYNTHESIS OF NEW 1,2,4-THIADIAZOLE AND 1,3,4-THIADIAZOLE BASED ACYCLIC NUCLEOSIDE ANALOGS WITH POTENTIAL ANTICANCER AND ANTIVIRAL ACTIVITY
    PARKANYI, C
    YUAN, HL
    CHO, NS
    JAW, JHJ
    WOODHOUSE, TE
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1988, 196 : 279 - ORGN
  • [45] ACTIVATED NITRILES IN HETEROCYCLIC SYNTHESIS .4. SYNTHESIS OF 1,3,4-THIADIAZOLE DERIVATIVES
    ELMOGHAYAR, MRH
    GHALI, EA
    RAMIZ, MMM
    ELNAGDI, MH
    LIEBIGS ANNALEN DER CHEMIE, 1985, (10): : 1962 - 1968
  • [46] Synthesis of Some Novel 1,3,4- and 1,2,4-Thiadiazole Derivatives
    Durust, Yasar
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2009, 184 (11) : 2923 - 2935
  • [47] 2,5-BIS(TRIFLUOROMETHYL)-1,3,4-OXADIAZOLE AND 2,5-BIS(TRIFLUOROMETHYL)-1,3,4-THIADIAZOLE AS ELECTRON-POOR DIAZADIENES IN THE DIELS-ALDER REACTION WITH INVERSE ELECTRON DEMAND
    SEITZ, G
    WASSMUTH, H
    CHEMIKER-ZEITUNG, 1988, 112 (02): : 80 - 81
  • [48] Synthesis and Biological Activities of 1,2,3-Thiadiazole Derivatives Containing 1,3,4-Thiadiazole Moiety
    Wang, Shouxin
    Zuo, Xiang
    Fan, Zhijin
    Zhang, Zhengcai
    Zhang, Jufang
    Xiong, Lixia
    Fu, Yifeng
    Fang, Zhen
    Wu, Qingjun
    Zhang, Youjun
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2013, 33 (11) : 2367 - 2375
  • [49] Synthesis and Antifungal Activity of 1,2,3-thiadiazole Derivatives Containing 1,3,4-thiadiazole Moiety
    Yan, Shui-Lin
    Yang, Ming-Yan
    Sun, Zhao-Hui
    Min, Li-Jing
    Tan, Cheng-Xia
    Weng, Jian-Quan
    Wu, Hong-Ke
    Liu, Xing-Hai
    LETTERS IN DRUG DESIGN & DISCOVERY, 2014, 11 (07) : 940 - 943
  • [50] Synthesis and Biological Activity of Acylthiourea Derivatives Contain 1,2,3-thiadiazole and 1,3,4-thiadiazole
    Yang, Ming-Yan
    Zhao, Wen
    Sun, Zhao-Hui
    Tan, Cheng-Xia
    Weng, Jian-Quan
    Liu, Xing-Hai
    LETTERS IN DRUG DESIGN & DISCOVERY, 2015, 12 (04) : 314 - 318
12345