Copper-Catalyzed Regio- and Stereoselective Sulfonylation of Alkynyl Imines with Sulfonyl Hydrazides: Access to (E)-β-Sulfonyl Enones

被引:3
作者
Chen, Rongxiang [1 ]
Li, Shaozhu [1 ]
Zhang, Jinju [1 ]
Cao, Jing [1 ]
Wang, Kai-Kai [1 ]
Meng, Tuanjie [2 ]
Liu, Lantao [2 ]
机构
[1] Xinxiang Univ, Sch Pharm, Xinxiang 453003, Peoples R China
[2] Shangqiu Normal Univ, Coll Chem & Chem Engn, Shangqiu 476000, Henan, Peoples R China
基金
中国国家自然科学基金;
关键词
VINYL SULFONES; BIOLOGICAL-ACTIVITY; ACRYLAMIDES; INHIBITORS; CHEMISTRY;
D O I
10.1021/acs.joc.2c01192
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A copper-catalyzed sulfonylation of alkynyl imines with sulfonyl hydrazides has been developed, which exhibited excellent regio- and stereoselectivity and furnished a series of (E)-beta-sulfonyl enones in moderate to good yields. Mechanistic studies suggest that this strategy goes through a radical process.
引用
收藏
页码:13322 / 13330
页数:9
相关论文
共 33 条
  • [11] The properties of unsaturated sulfur compounds I Alpha beta unsaturated sulfones
    Kohler, EP
    Potter, H
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1935, 57 : 1316 - 1321
  • [12] Copper-Catalyzed Three Component Regio- and Stereospecific Selenosulfonation of Alkynes: Synthesis of (E)-β-Selenovinyl Sulfones
    Liu, Yang
    Zheng, Guangfan
    Zhang, Qian
    Li, Yan
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (04) : 2269 - 2275
  • [13] Transition-metal mediated carbon-sulfur bond activation and transformations: an update
    Lou, Jiang
    Wang, Quannan
    Wu, Ping
    Wang, Hongmei
    Zhou, Yong-Gui
    Yu, Zhengkun
    [J]. CHEMICAL SOCIETY REVIEWS, 2020, 49 (13) : 4307 - 4359
  • [14] Vinyl sulfones: Synthetic preparations and medicinal chemistry applications
    Meadows, D. Christopber
    Gervay-Hague, Jacquelyn
    [J]. MEDICINAL RESEARCH REVIEWS, 2006, 26 (06) : 793 - 814
  • [15] Ring substituent effects on biological activity of vinyl sulfones as inhibitors of HIV-1
    Meadows, D. Christopher
    Sanchez, Tino
    Neamati, Nouri
    North, Thomas W.
    Gervay-Hague, Jacquelyn
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2007, 15 (02) : 1127 - 1137
  • [16] A Coumarin- Labeled Vinyl Sulfone as Tripeptidomimetic Activity- Based Probe for Cysteine Cathepsins
    Mertens, Matthias D.
    Schmitz, Janina
    Horn, Martin
    Furtmann, Norbert
    Bajorath, Juergen
    Mares, Michael
    Guetschow, Michael
    [J]. CHEMBIOCHEM, 2014, 15 (07) : 955 - 959
  • [17] COPPER-CATALYZED REACTION OF TERMINAL ALKYNES WITH NITRONES - SELECTIVE SYNTHESIS OF 1-AZA-1-BUTEN-3-YNE AND 2-AZETIDINONE DERIVATIVES
    MIURA, M
    ENNA, M
    OKURO, K
    NOMURA, M
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (16) : 4999 - 5004
  • [18] Oxidative Coupling with S-N Bond Formation
    Mulina, Olga M.
    Ilovaisky, Alexey I.
    Terent'ev, Alexander O.
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (34) : 4648 - 4672
  • [19] Conjugated Ynones in Organic Synthesis
    Najera, Carmen
    Sydnes, Leiv K.
    Yus, Miguel
    [J]. CHEMICAL REVIEWS, 2019, 119 (20) : 11110 - 11244
  • [20] The chemistry of sulfinyl and sulfonyl enones
    Nenajdenko, Valentine G.
    Krasovskiy, Arkady L.
    Balenkova, Elizabeth S.
    [J]. TETRAHEDRON, 2007, 63 (51) : 12481 - 12539