One-Pot Synthesis of N-Substituted Enaminones from Ketones, Aromatic Nitriles and Halides

被引:4
作者
Duan, Xiyan [1 ]
Yang, Shijie [1 ]
Yao, Changyang [1 ]
Jia, Fenglin [1 ]
Wang, Lin [1 ]
Li, Weinan [1 ]
Meng, Zhen [1 ]
Zhou, Yingying [1 ]
Li, Xiaoqing [1 ]
机构
[1] Henan Univ Sci & Technol, Sch Chem Engn & Pharmaceut, 263 Kaiyuan Rd, Luolong Dist, Luoyang, Peoples R China
关键词
One-pot Synthesis; N-Substituted Enaminones; aldol reaction; Ullmann reaction; H FUNCTIONALIZATION SYNTHESIS; ALPHA; BETA-UNSATURATED KETONES; ESTERS; CYCLIZATION; EFFICIENT; INDOLES;
D O I
10.1002/slct.201903695
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A simple and convenient one-pot copper-catalyzed synthesis of N-substituted enaminones has been demonstrated from ketones, aromatic nitriles and halides. This transformation involves the aldol-type reaction and Ullmann-type cross coupling, which features high efficient and inexpensive Cu-catalyst with broader diversification scope.
引用
收藏
页码:12992 / 12995
页数:4
相关论文
共 42 条
[21]   TBAI-catalyzed selective synthesis of sulfonamides and β-aryl sulfonyl enamines: coupling of arenesulfonyl chlorides and sodium sulfinates with tert-amines [J].
Jiang, Hongmei ;
Tang, Xiaoyue ;
Xu, Zhihui ;
Wang, Huixian ;
Han, Kang ;
Yang, Xiaolan ;
Zhou, Yuanyuan ;
Feng, Yong-Lai ;
Yu, Xian-Yong ;
Gui, Qingwen .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (10) :2715-2720
[22]   New entry to a three-component pyrimidine synthesis by TMS-ynones via Sonogashira coupling [J].
Karpov, AS ;
Muller, TJJ .
ORGANIC LETTERS, 2003, 5 (19) :3451-3454
[23]   Cu(OAc)2/TFA-Promoted Formal [3+3] Cycloaddition/Oxidation of Enamines and Enones for Synthesis of Multisubstituted Aromatic Amines [J].
Li, Liang ;
Zhao, Mi-Na ;
Ren, Zhi-Hui ;
Li, Jian-Li ;
Guan, Zheng-Hui .
ORGANIC LETTERS, 2012, 14 (13) :3506-3509
[24]   Copper-Catalyzed Synthesis of Multisubstituted Indoles through Tandem Ullmann-Type C-N Formation and Cross-dehydrogenative Coupling Reactions [J].
Li, Yue ;
Peng, Jinsong ;
Chen, Xin ;
Mo, Baichuan ;
Li, Xue ;
Sun, Peng ;
Chen, Chunxia .
JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (09) :5288-5294
[25]   Iodine/Copper Iodide-Mediated C-H Functionalization: Synthesis of Imidazo[1,2-a]pyridines and Indoles from N-Aryl Enamines [J].
Liu, Jing ;
Wei, Wei ;
Zhao, Ting ;
Liu, Xuanyu ;
Wu, Jie ;
Yu, Wenquan ;
Chang, Junbiao .
JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (19) :9326-9336
[26]   Emergence of Copper-Mediated Formation of C-C Bonds [J].
Maaliki, Carine ;
Thiery, Emilie ;
Thibonnet, Jerome .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (02) :209-228
[27]   STABILITIES OF BIVALENT METAL COMPLEXES OF SOME B-KETOIMINES [J].
MARTIN, DF ;
MARTIN, BB ;
JANUSONIS, GA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1961, 83 (01) :73-+
[28]  
SAKAMOTO T, 1990, SYNTHESIS-STUTTGART, P215
[29]   DM27, an enaminone, modifies the in vitro transport of antiviral therapeutic agents [J].
Salama, NN ;
Kenneth, RSB ;
Eddington, ND .
BIOPHARMACEUTICS & DRUG DISPOSITION, 2004, 25 (05) :227-236
[30]   Copper catalysed Ullmann type chemistry: from mechanistic aspects to modern development [J].
Sambiagio, Carlo ;
Marsden, Stephen P. ;
Blacker, A. John ;
McGowan, Patrick C. .
CHEMICAL SOCIETY REVIEWS, 2014, 43 (10) :3525-3550