Substrate-controlled and highly stereoselective synthesis of 2-aminobut-2-ene-1, 4-diones

被引:14
|
作者
Deng, Cong [1 ]
Yang, Yan [1 ]
Gao, Meng [1 ]
Zhu, Yan-Ping [1 ]
Wu, An-Xin [1 ]
Ma, Jun-Rui [2 ]
Yin, Guo-Dong [2 ]
机构
[1] Cent China Normal Univ, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Peoples R China
[2] Hubei Normal Univ, Hubei Key Lab Pollutant Anal & Reuse Technol, Huangshi 435002, Peoples R China
基金
中国国家自然科学基金;
关键词
Aryl methyl ketones; Amines; 2-Aminobut-2-ene-1,4-diones; Substrate-controlled; Z/E-Stereoselectivity; UNSYMMETRICAL BIARYLS; ADDITION-REACTIONS; TRANSFORMATION; DERIVATIVES; STRATEGY; 1,4-DIARYL-2-(ARYLAMINO)BUT-2-ENE-1,4-DIONES; DIBENZOYLACETYLENE; 2H-PYRAN-2-ONES; REARRANGEMENTS; REACTIVITY;
D O I
10.1016/j.tet.2012.03.049
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
2-Methylthio-substituted 1,4-enediones, obtained from readily available aryl methyl ketones, were reacted with primary or secondary amines to afford the desired 1,4-diaryl-2-aminobut-2-ene-1,4-diones in excellent yields with high Z/E-stereoselectivity. (C) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码:3828 / 3834
页数:7
相关论文
共 50 条
  • [21] Synthesis of new 1,3,3-triarylspiro [azetidin-2,3′-indoline]-2′,4-diones
    Singh, GS
    INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY, 2001, 10 (03) : 235 - 236
  • [22] NOVEL SYNTHESIS OF HEXAHYDROAZEPINE 2,4-DIONES - SYNTHESIS AND REARRANGEMENT OF 3-ALKOXY-2-CYCLOHEXEN-1-ONE OXIME
    TAMURA, Y
    KITA, Y
    MATSUTAK.Y
    TERASHIM.M
    CHEMISTRY & INDUSTRY, 1970, (42) : 1350 - &
  • [23] Highly stereo-selective synthesis of (Z)-2,3-diiodo-1,4diarylbut-2-ene-1,4-diones via oxidative iodination of 1,4-diarylbuta-1,3-diynes
    Singha, Raju
    Dhara, Shubhendu
    Ray, Jayanta K.
    RSC ADVANCES, 2013, 3 (46): : 23989 - 23992
  • [24] Synthesis of 6-arylspiro[tetrahydropyran-3,1′-cyclobutane]-2,4-diones
    N. F. Kirillov
    V. V. Shchepin
    V. S. Melekhin
    Russian Journal of Organic Chemistry, 2007, 43 : 1628 - 1631
  • [25] Synthesis of Bis(1,2,3-Triazole) Functionalized Quinoline-2,4-Diones
    Milicevic, David
    Kimmel, Roman
    Gazvoda, Martin
    Urankar, Damijana
    Kafka, Stanislav
    Kosmrlj, Janez
    MOLECULES, 2018, 23 (09):
  • [26] Oxidative acylation of ,-diarylallylic alcohols: Synthesis of 1,2,4-triarylbutane-1,4-diones
    Li, Yong
    Leng, Yuting
    Wang, Shiwei
    Gao, Yuhui
    Lv, Huiyan
    Chang, Junbiao
    Wu, Yusheng
    Wu, Yangjie
    APPLIED ORGANOMETALLIC CHEMISTRY, 2018, 32 (08)
  • [27] Synthesis of 6-arylspiro[tetrahydropyran-3,1′-cyclobutane]-2,4-diones
    Kirillov, N. F.
    Shchepin, V. V.
    Melekhin, V. S.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 43 (11) : 1628 - 1631
  • [28] HIGHLY STEREOSELECTIVE CHELATION CONTROLLED ENE-REACTION OF 2-(ALKYLTHIO)ALLYL SILYL ETHERS
    NAKAMURA, T
    TANINO, K
    KUWAJIMA, I
    TETRAHEDRON LETTERS, 1993, 34 (03) : 477 - 480
  • [29] Highly selective Synthesis of 1-Phenylpentane-1, 4-Diones, and (E)-5-Hydroxy-5-phenylpent-3-en-2-ones Catalyzed by Organophosphorus Compounds
    Zhang, Qing
    Qiao, Yan-Fei
    Huang, Min
    Liang, Hong-Dong
    Zhou, Ru-Jin
    HETEROATOM CHEMISTRY, 2009, 20 (07) : 425 - 430
  • [30] Tunable Synthesis of 2-Ene-1,4-diones, 4-Hydroxycyclopent-2-en-1-ones, and 2-(Furan-3-yl)acetamides via Palladium-Catalyzed Cascade Reactions of Allenols
    He, Yan
    Zheng, Zhi
    Liu, Qimeng
    Song, Guixian
    Sun, Nan
    Chai, Xinyuan
    JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (20): : 12514 - 12526