Making Flavone Thioethers Using Halides and Powdered Sulfur or Na2S2O3

被引:26
|
作者
Tang, Qiujie [1 ]
Bian, Zhaogang [1 ]
Wu, Wei [1 ]
Wang, Jin [1 ]
Xie, Ping [2 ]
Pittman, Charles U., Jr. [3 ]
Zhou, Aihua [1 ]
机构
[1] Jiangsu Univ, Pharm Sch, Xuefu Rd 301, Zhenjiang City 212013, Jiangsu, Peoples R China
[2] Jiangsu Univ Lib, Sci Informat Res Inst, Xuefu Rd 301, Zhenjiang City 212013, Jiangsu, Peoples R China
[3] Mississippi State Univ, Mississippi State, MS 39762 USA
来源
JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 82卷 / 19期
关键词
C-H FUNCTIONALIZATION; METAL-FREE CONDITIONS; S BOND FORMATION; ENANTIOSELECTIVE SULFENYLATION; ARYLSULFONYL CHLORIDES; DIARYL CHALCOGENIDES; CATALYZED SYNTHESIS; AMMONIUM IODIDE; DERIVATIVES; THIOLATION;
D O I
10.1021/acs.joc.7b01320
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The method for constructing C-S bonds is very important in organic synthesis. Here a new sulfenylation method to generate flavone thioether derivatives was developed by employing aromatic or alkyl halides, S powder and Na2S2O3 as reactants. Good yields of regioselective C-alkyl-S and C-aryl S-substituted flavones were generated under relatively environmentally friendly and simple conditions. This method might be potentially applicable to large scale production, and it enriches current sulfenylation methods.
引用
收藏
页码:10617 / 10622
页数:6
相关论文
共 50 条
  • [1] Cu-catalyzed sulfenylation of imidazol[1,2-a]pyridine via C-H functionalization using a combination of Na2S2O3 and halides
    Ding, Yingcai
    Xie, Ping
    Zhu, Wenhui
    Xu, Baojun
    Zhao, Wannian
    Zhou, Aihua
    RSC ADVANCES, 2016, 6 (85): : 81932 - 81935
  • [2] Direct Synthesis of Diverse 2-Aminobenzo[b]thiophenes via Palladium-Catalyzed Carbon-Sulfur Bond Formation Using Na2S2O3 as the Sulfur Source
    Hou, Chuanwei
    He, Qian
    Yang, Chunhao
    ORGANIC LETTERS, 2014, 16 (19) : 5040 - 5043
  • [3] Hydroxymethylation of Quinolines with Na2S2O8 by a Radical Pathway
    Zhou, Luan
    Okugawa, Naoyuki
    Togo, Hideo
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (41) : 6239 - 6245
  • [4] One-Pot Synthesis of 2-R-Naphtho[2,3-b]thiophene-4,9-diones via Cyclization of 2-(R-Ethynyl)-1,4-naphthoquinones with Na2S2O3
    Baranov, Denis S.
    Popov, Alexander A.
    Nevostruev, Danil A.
    Dmitriev, Alexey A.
    Gatilov, Yurii, V
    Kobeleva, Elena S.
    JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (17): : 11361 - 11369
  • [5] K2S2O8-Mediated halogenation of 2-arylimidazo[1,2-α]pyridines using sodium halides as the halogen sources
    Katrun, Praewpan
    Kuhakarn, Chutima
    TETRAHEDRON LETTERS, 2019, 60 (14) : 989 - 993
  • [6] Pd-Catalyzed Selective Synthesis of Cyclic Sulfonamides and Sulfinamides Using K2S2O5 as a Sulfur Dioxide Surrogate
    Konishi, Hideyuki
    Tanaka, Hiromichi
    Manabe, Kei
    ORGANIC LETTERS, 2017, 19 (07) : 1578 - 1581
  • [7] Synthesis and structure of [Na(15-crown-5)][Ph2P(S)OB(C6F5)3] and [Na(15-crown-5)2][Ph2P(S)O•••HO(S)PPh2]
    Kather, Ralf
    Lork, Enno
    Rat, Ciprian-Ionut
    Silvestru, Cristian
    Beckmann, Jens
    MAIN GROUP METAL CHEMISTRY, 2017, 40 (1-2) : 47 - 51
  • [8] AgSCF3/Na2S2O8-Promoted Trifluoromethylthiolation/Cyclization of o-Propargyl Arylazides/o-Alkynyl Benzylazides: Synthesis of SCF3-Substituted Quinolines and Isoquinolines
    Qiu, Yi-Feng
    Niu, Yue-Jie
    Wei, Xi
    Cao, Bao-Qian
    Wang, Xi-Cun
    Quan, Zheng-Jun
    JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (07): : 4165 - 4178
  • [9] Comparative studies on the bioactivity of some borate glasses and glass-ceramics from the two systems: Na2O-CaO-B2O3 and NaF-CaF2-B2O3
    ElBatal, Fatma H.
    Ouis, Mona A.
    ElBatal, Hatem A.
    CERAMICS INTERNATIONAL, 2016, 42 (07) : 8247 - 8256
  • [10] Synthesis of Diversified Thioethers, 1-Aroylalkylisoquinolin-1-yl Thioethers, by Electrophilic S-Alkylation of 3-Phenyl Isoquinoline-1(2H)-thione
    Manivel, P.
    Khan, F. Nawaz
    Hatwar, Venkatesha R.
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2010, 185 (09) : 1932 - 1942