Synthesis of Indole-2-methylsulfonamides by Domino Sonogashira Coupling and Hydroamination Reaction

被引:5
|
作者
Debnath, Sudarshan [1 ,2 ]
Malakar, Suniti [1 ,2 ]
Mondal, Shovan [1 ,2 ]
机构
[1] Syamsundar Coll, Dept Chem, Shyamsundar 713424, India
[2] Visva Bharati Univ, Dept Chem, Santini Ketan 731235, W Bengal, India
来源
CHEMISTRYSELECT | 2017年 / 2卷 / 10期
关键词
Domino reaction; Hydroamination reaction; Indole; Sonogashira coupling; Sulfonamide; PALLADIUM-CATALYZED SYNTHESIS; ELECTROPHILIC CYCLIZATION; REGIOSELECTIVE SYNTHESIS; HETEROANNULATION REACTION; PROPARGYLIC AMINES; HECK CYCLIZATION; FUSED SULTONES; INDOLES; COPPER; 2-(AMINOMETHYL)INDOLES;
D O I
10.1002/slct.201700544
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A domino Sonogashira coupling and hydroamination reaction between o-iodo-N, N-dimethylaniline derivatives and propargyl sulfonamides are described. This protocol allows access to a variety of indole-2-methylsulfonamides in good to excellent yields. The structures of the synthesized compounds are confirmed by XRD studies.
引用
收藏
页码:3147 / 3151
页数:5
相关论文
共 50 条
  • [21] Synthesis of α-Alkynyl-β,β,β-trifluoroalanine Derivatives by Sonogashira Cross-Coupling Reaction
    Shchetnikov, Grigorii T.
    Zotova, Maria A.
    Bruneau, Christian
    Dixneuf, Pierre H.
    Osipov, Sergey N.
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (08) : 1587 - 1592
  • [23] Synthesis of indole derivatives by domino hydroformylation/indolization of 2-nitrocinnamaldehydes
    Marchetti, M.
    Paganelli, S.
    Carboni, D.
    Ulgheri, F.
    Del Ponte, G.
    [J]. JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2008, 288 (1-2) : 103 - 108
  • [24] Convenient indole synthesis from 2-iodoanilines and terminal alkynes by the sequential Sonogashira reaction and the cyclization reaction promoted by tetrabutylammonium fluoride (TBAF)
    Suzuki, N
    Yasaki, S
    Yasuhara, A
    Sakamoto, T
    [J]. CHEMICAL & PHARMACEUTICAL BULLETIN, 2003, 51 (10) : 1170 - 1173
  • [25] Synthesis of Unexpected Pyrrolo[2,3-b]quinoxaline-2-carbaldehydes via Sonogashira Coupling Reaction
    Keivanloo, Ali
    Bakherad, Mohammad
    Rahimi, Amin
    [J]. SYNTHESIS-STUTTGART, 2010, (10): : 1599 - 1602
  • [26] Palladium(<sc>ii</sc>) complexes bearing mesoionic carbene ligands: catalytic application in domino Sonogashira coupling/cyclization reactions for one-pot synthesis of benzofuran and indole derivatives
    Joshi, Om Prakash
    Thirumoorthi, Ramalingam
    Pardasani, Ram T.
    Ray, Sriparna
    Dash, Chandrakanta
    [J]. RSC ADVANCES, 2024, 14 (37) : 27141 - 27152
  • [27] Unexpected tandem Sonogashira-carbopalladation-Sonogashira coupling reaction of benzyl halides with terminal alkynes: A novel four-component domino sequence to highly substituted enynes
    Pottier, LR
    Peyrat, JF
    Alami, M
    Brion, JD
    [J]. SYNLETT, 2004, (09) : 1503 - 1508
  • [28] Copper-Catalyzed Tandem Imine Formation, Sonogashira Coupling and Intramolecular Hydroamination: A Facile Synthesis of 3-Aryl-γ-carbolines
    Dhiman, Shiv
    Rhodes, Steven
    Kumar, Dalip
    Kumar, Anil
    Jha, Mukund
    [J]. CHEMISTRYSELECT, 2017, 2 (28): : 8922 - 8926
  • [29] An Efficient Synthesis of New Pyrazole-Linked Oxazoles via Sonogashira Coupling Reaction
    Tamardash, Leila Kamrani
    Bakherad, Mohammad
    Keivanloo, Ali
    Notash, Behrouz
    [J]. CHEMISTRYSELECT, 2023, 8 (18):
  • [30] One-pot synthesis of symmetrical and unsymmetrical bisarylethynes by a modification of the Sonogashira coupling reaction
    Mio, MJ
    Kopel, LC
    Braun, JB
    Gadzikwa, TL
    Hull, KL
    Brisbois, RG
    Markworth, CJ
    Grieco, PA
    [J]. ORGANIC LETTERS, 2002, 4 (19) : 3199 - 3202