A Metal-Free Sulfenylation and Bromosulfenylation of Indoles: Controllable Synthesis of 3-Arylthioindoles and 2-Bromo-3-arylthioindoles

被引:133
作者
Huang, Dayun [1 ]
Chen, Jiuxi [1 ]
Dan, Weixing [1 ]
Ding, Jinchang [1 ,2 ]
Liu, Miaochang [1 ]
Wu, Huayue [1 ]
机构
[1] Wenzhou Univ, Coll Chem & Mat Engn, Wenzhou 325035, Peoples R China
[2] Wenzhou Vocat & Tech Coll, Coll Light Ind, Wenzhou 325035, Peoples R China
基金
中国国家自然科学基金;
关键词
3-arylthioindoles; 2-bromo-3-arylthioindoles; bromosulfenylation; metal-free conditions; sulfenylation; EFFICIENT SULFENYLATION; CATALYZED SULFENYLATION; QUINONE MONO-O; S-ACETALS; POTENT INHIBITORS; 2ND SULFENYLATION; ARYL SULFONES; 3-SULFENYL; DISULFIDES; 3-SELENYLINDOLES; ARYLTHIOINDOLES;
D O I
10.1002/adsc.201200227
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
An efficient metal-free sulfenylation of indoles with disulfides has been developed, leading to 3-arylthioindoles in moderate to excellent yields. Furthermore, bromosulfenylation of indoles with disulfides has been realized for the first time providing a new family of 2-bromo-3-arylthioindole derivatives in good yield by the one-pot construction of C-S and C-Br bonds. It is noteworthy that the system enables the use of both the RS moieties in RSSR and shows a broad functional group tolerance.
引用
收藏
页码:2123 / 2128
页数:6
相关论文
共 52 条
  • [11] A new odorless one-pot synthesis of thioesters and selenoesters promoted by Rongalite®
    Dan, Weixing
    Deng, Hongjuan
    Chen, Jiuxi
    Liu, Miaochang
    Ding, Jinchang
    Wu, Huayue
    [J]. TETRAHEDRON, 2010, 66 (37) : 7384 - 7388
  • [12] New arylthioindoles: Potent inhibitors of tubulin polymerization. 2. Structure-activity relationships and molecular modeling studies
    De Martino, G
    Edler, MC
    La Regina, G
    Coluccia, A
    Barbera, MC
    Barrow, D
    Nicholson, RI
    Chiosis, G
    Brancale, A
    Hamel, E
    Artico, M
    Silvestri, R
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2006, 49 (03) : 947 - 954
  • [13] Arylthioindoles, potent inhibitors of tubulin polymerization
    De Martino, G
    La Regina, G
    Coluccia, A
    Edler, MC
    Barbera, MC
    Brancale, A
    Wilcox, E
    Hamel, E
    Artico, M
    Silvestri, R
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2004, 47 (25) : 6120 - 6123
  • [14] Iron-Catalyzed Sulfenylation of Indoles with Disulfides Promoted by a Catalytic Amount of Iodine
    Fang, Xiao-Li
    Tang, Ri-Yuan
    Zhong, Ping
    Li, Jin-Heng
    [J]. SYNTHESIS-STUTTGART, 2009, (24): : 4183 - 4189
  • [15] Rongalite® promoted highly regioselective synthesis of β-hydroxy sulfides by ring opening of epoxides with disulfides
    Guo, Wenxue
    Chen, Jiuxi
    Wu, Dengze
    Ding, Jinchang
    Chen, Fan
    Wu, Huayue
    [J]. TETRAHEDRON, 2009, 65 (27) : 5240 - 5243
  • [16] Palladium-Catalyzed Annulation of 2-(1-Alkynyl)benzenamines with Disulfides: Synthesis of 3-Sulfenylindoles
    Guo, Yan-Jin
    Tang, Ri-Yuan
    Li, Jin-Heng
    Zhong, Ping
    Zhang, Xing-Guo
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (16) : 2615 - 2618
  • [17] Regioselective synthesis of mixed indole 2,3-bis(sulfides). A study of the mechanism of the second sulfenylation of indole
    Hamel, P
    Preville, P
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (05) : 1573 - 1577
  • [18] Mechanism of the second sulfenylation of indole
    Hamel, P
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (09) : 2854 - 2858
  • [19] CHLOROSULFENYLATION-DEHYDROCHLORINATION REACTIONS - NEW AND IMPROVED METHODOLOGY FOR SYNTHESIS OF UNSATURATED ARYL SULFIDES AND ARYL SULFONES
    HOPKINS, PB
    FUCHS, PL
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (06) : 1208 - 1217
  • [20] Synthesis of Carbazoles and 1,2-Dihydrocarbazoles by Domino 'Twofold Heck-6π-Electrocyclization' Reactions of Di- and Tribromo-N-methylindoles
    Hussain, Munawar
    Tung, Dang Thanh
    Langer, Peter
    [J]. SYNLETT, 2009, (11) : 1822 - 1826