Water-Promoted Synthesis of Enaminones: Mechanism Investigation and Application in Multicomponent Reactions

被引：54
|
作者：
Liu, Yunyun [1 ]
Zhou, Rihui [1 ]
Wan, Jie-Ping [1 ]
机构：
[1] Jiangxi Normal Univ, Coll Chem & Chem Engn, Nanchang 330022, Peoples R China
来源：
SYNTHETIC COMMUNICATIONS | 2013年 / 43卷 / 18期
关键词：
Enaminone; green synthesis; mechanism; multicomponent; water promotion; AMINES; ESTERS; ALPHA; ACID;
D O I：
10.1080/00397911.2012.715712
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Highly stereoselective synthesis of Z-enaminones bearing reactive secondary amino group has been successfully performed in water using tertiary amino group functionalized enaminones under ambient conditions. An interesting promotion effect of water on the reaction via hydrolysis-dehydration condensation has been observed through a designed isotope labeling experiment. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) to view the free supplemental file.
引用
收藏
页码：2475 / 2483
页数：9
相关论文
共 50 条
  • [1] WATER-PROMOTED ORGANIC-REACTIONS
    LUBINEAU, A
    AUGE, J
    QUENEAU, Y
    SYNTHESIS-STUTTGART, 1994, (08): : 741 - 760
  • [2] Water-Promoted Green Synthesis of Heteroaryl Thioether
    Ma Xiantao
    Yan Xiaoyu
    Zhu Yingying
    Niu Shuanglin
    Wang Yuxuan
    Yuan Chao
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2023, 43 (06) : 2136 - 2142
  • [3] Water-promoted C-S bond formation reactions
    Xie, Peizhong
    Wang, Jinyu
    Liu, Yanan
    Fan, Jing
    Wo, Xiangyang
    Fu, Weishan
    Sun, Zuolian
    Loh, Teck-Peng
    NATURE COMMUNICATIONS, 2018, 9
  • [4] Preadsorbed Water-Promoted Mechanism of the Water-Gas Shift Reaction
    Zeinalipour-Yazdi, Constantinos D.
    Efstathiou, Angelos M.
    JOURNAL OF PHYSICAL CHEMISTRY C, 2008, 112 (48): : 19030 - 19039
  • [5] Water-promoted C-S bond formation reactions
    Peizhong Xie
    Jinyu Wang
    Yanan Liu
    Jing Fan
    Xiangyang Wo
    Weishan Fu
    Zuolian Sun
    Teck-Peng Loh
    Nature Communications, 9
  • [6] Uncovering the mechanism of water-promoted electrochemical degradation of NiSalen polymers
    V. Alekseeva, Elena
    Vereshchagin, Anatoliy A.
    V. Novozhilova, Maria
    Panjwani, Naitik A.
    V. Novoselova, Julia
    Lukyanov, Daniil A.
    V. Beletskii, Evgenii
    Behrends, Jan
    V. Sizov, Vladimir
    Levin, Oleg, V
    JOURNAL OF ELECTROANALYTICAL CHEMISTRY, 2023, 935
  • [7] ON THE WATER-PROMOTED MECHANISM OF PEPTIDE CLEAVAGE BY CARBOXYPEPTIDASE-A - A THEORETICAL-STUDY
    ALVAREZSANTOS, S
    GONZALEZLAFONT, A
    LLUCH, JM
    OLIVA, B
    AVILES, FX
    CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1994, 72 (10): : 2077 - 2083
  • [8] Reverse Hydrogen Spillover on Metal Oxides for Water-Promoted Catalytic Oxidation Reactions
    Fu, Hao
    Liu, Hongjie
    Wang, Xiyang
    Zhang, Wenhua
    Zhang, Hui
    Luo, Yunhong
    Deng, Xianwang
    King, Graham
    Chen, Ning
    Wang, Liwei
    Wu, Yimin A.
    ADVANCED MATERIALS, 2024, 36 (36)
  • [9] WATER-PROMOTED ORGANIC-REACTIONS - ALDOL REACTION UNDER NEUTRAL CONDITIONS
    LUBINEAU, A
    JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (11): : 2142 - 2144
  • [10] Water-Promoted Synthesis of 3,3′-Di(indolyl)oxindoles
    Deb, Mohit L.
    Bhuyan, Pulak J.
    SYNTHETIC COMMUNICATIONS, 2009, 39 (12) : 2240 - 2243
12345