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
来源：
TETRAHEDRON | 2012年 / 68卷 / 20期
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
  • [1] Simple, efficient, and stereoselective oxidation of triphenylfurans to cis-but-2-ene-1,4-diones
    Rappai, John P.
    Prathapan, Sreedharan
    Vishnu Unni, Manthitta V.
    Unnikrishnan, Perupparampil A.
    SYNTHETIC COMMUNICATIONS, 2007, 37 (4-6) : 569 - 572
  • [2] Substrate-controlled chemoselective synthesis of 1-sulfonylquinazoline-2,4(1H,3H)-diones and 2-sulfonamidobenzonitriles
    Zhao, Ping
    Zeng, Qingle
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2023, 60 (11) : 1938 - 1944
  • [3] SYNTHESIS, STRUCTURE, AND REACTIVITY OF 1,4-DIARYL-2-(ARYLAMINO)BUT-2-ENE-1,4-DIONES
    PARADISI, C
    PRATO, M
    QUINTILY, U
    SCORRANO, G
    JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (25): : 5156 - 5159
  • [4] Highly stereoselective synthesis of aminoglycosides via rhodium-catalyzed and substrate-controlled aziridination of glycals
    Lorpitthaya, Rujee
    Sophy, K. B.
    Kuo, Jer-Lai
    Liu, Xue-Wei
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2009, 7 (07) : 1284 - 1287
  • [5] Synthesis and substrate-controlled reactions of 2,2'-unsaturated biquinazolinones
    Pertusati, Fabrizio
    Nutz, Eva
    Kariuki, Benson M.
    Coogan, Michael P.
    TETRAHEDRON, 2017, 73 (01) : 55 - 63
  • [6] FACILE SYNTHESIS OF FURANS FROM 2-ENE-1,4-DIONES BY DIPHOSPHORUS TETRAIODIDE
    DEMIRDJI, SH
    HADDADIN, MJ
    ISSIDORIDES, CH
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1985, 22 (02) : 495 - 496
  • [7] NHC-catalysed annulation of enals to ene-1,4-diones: stereoselective synthesis of 1,3-diaryl-4-acyl cyclopentenes
    Paul, Rony Rajan
    Lakshmi, K. C. Seetha
    Suresh, Eringathodi
    Nair, Vijay
    TETRAHEDRON LETTERS, 2013, 54 (16) : 2046 - 2049
  • [8] Stereoselective Synthesis of cis-2-Ene-1,4-diones via Aerobic Oxidation of Substituted Furans Catalyzed by ABNO/HNO3
    Yang, Liqun
    Wang, Jingyang
    Wang, Yue
    Li, Xiaotong
    Liu, Wei
    Zhang, Zhaoguo
    Xie, Xiaomin
    JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (21): : 14311 - 14320
  • [9] A novel β-(oxy)alkyl radical during copper(I)-mediated stereoselective synthesis of (Z)-ene-1,4-diones in a reaction of 2,2,2-trichloro-1-phenylethanone
    Ram, Ram N.
    Tittal, Ram K.
    TETRAHEDRON LETTERS, 2016, 57 (22) : 2437 - 2440
  • [10] [2 + 2]CYCLOADDITIONS OF TETRAALKOXYETHYLENES WITH KETENES - GENERAL ROUTE TO 2-SUBSTITUTED 1-HYDROXYCYCLOBUT-1-ENE-3,4-DIONES
    BELLUS, D
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (25) : 8026 - 8028
12345