Synthesis of Tetrasubstituted Enamines Using Secondary Amines and In Situ-Generated Allenes from Nitrocyclopropanes

被引:0
|
作者
Xu, Zhong-Yang [1 ]
Wei, Jian-Sheng [1 ]
Liu, Li [2 ]
Hu, Qing-Bo [1 ]
Zhu, Jin-Yao [1 ]
Zhou, Zhan-Yu [1 ]
Xia, Ai-Bao [1 ]
Xu, Dan-Qian [1 ]
机构
[1] Zhejiang Univ Technol, Catalyt Hydrogenat Res Ctr, State Key Lab Breeding Base Green Chem Synth Techn, Hangzhou 310014, Peoples R China
[2] Hangzhou Guangcheng Energy & Environm Technol Co L, Hangzhou 310006, Peoples R China
来源
JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 89卷 / 19期
基金
浙江省自然科学基金;
关键词
STEREOSELECTIVE-SYNTHESIS; ASYMMETRIC-SYNTHESIS; MOLECULAR-OXYGEN; ALKENES; ACCESS; ESTERS; CYCLOPROPANES; CARZINOPHILIN; DERIVATIVES; REACTIVITY;
D O I
10.1021/acs.joc.4c00829
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel reaction of cyclic and acyclic secondary amines with in situ-generated allene intermediate species from nitro-substituted donor-acceptor cyclopropanes is reported. In the presence of a simple inorganic base, NaOH, tetrasubstituted enamine derivatives can be obtained in moderate to excellent yields. The reaction is operationally easy, features mild reaction conditions and simple inorganic bases, and is free of transition metals.
引用
收藏
页码:13868 / 13875
页数:8
相关论文
共 50 条
  • [1] In situ generation of highly reactive allenes from nitrocyclopropanes: controllable synthesis of enynes and enesters
    Zhou, Zhan-Yu
    Xu, Zhong-Yang
    Shen, Qiao-Yu
    Huang, Li-Sha
    Zhang, Xing
    Xia, Ai-Bao
    Xu, Dan-Qian
    Xu, Zhen-Yuan
    CHEMICAL COMMUNICATIONS, 2021, 57 (52) : 6424 - 6427
  • [2] A Cascade Synthesis of Aminohydantoins Using In Situ-Generated N-Substituted Isocyanates
    Vincent-Rocan, Jean-Francois
    Clavette, Christian
    Leckett, Kyle
    Beauchemin, Andre M.
    CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (10) : 3886 - 3890
  • [3] Synthesis of Chamaecypanone C Analogues from in Situ-Generated Cyclopentadienones and Their Biological Evaluation
    Dong, Suwei
    Qin, Tian
    Hamel, Ernest
    Beutler, John A.
    Porco, John A., Jr.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (48) : 19782 - 19787
  • [4] Selective Oxidation Using In Situ-Generated Hydrogen Peroxide
    Lewis, Richard J.
    Hutchings, Graham J.
    ACCOUNTS OF CHEMICAL RESEARCH, 2023, 57 (01) : 106 - 119
  • [5] SYNTHESIS OF ENAMINES FROM CYCLOALKANONES AND SECONDARY CYCLIC AMINES USING K-10 MONTMORILLONITE CLAY
    DEWAN, SK
    VARMA, U
    MALIK, SD
    JOURNAL OF CHEMICAL RESEARCH, 1995, (01) : 21 - 21
  • [6] A facile and convenient synthesis of disarmed glycosyl fluorides using in situ-generated iodine monofluoride
    Mugunthan, G.
    Kartha, K. P. Ravindranathan
    TETRAHEDRON LETTERS, 2012, 53 (42) : 5631 - 5634
  • [7] Benzothiazole Synthesis: Mechanistic Investigation of an In Situ-Generated Photosensitizing Disulfide
    Hwang, Ho Seong
    Lee, Sumin
    Han, Sung Su
    Moon, Yu Kyung
    You, Youngmin
    Cho, Eun Jin
    JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (18): : 11835 - 11843
  • [8] Catalytic stereoselective synthesis of cyclopentanones from donor-acceptor cyclopropanes and in situ-generated ketenes
    Mitra, Shubhanjan
    Connolly, Sophie M.
    Ayidi, Saud
    Mondal, Mukulesh
    Panda, Manashi
    Kelly, Brian G.
    Kerrigan, Nessan J.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2024, 22 (35) : 7128 - 7132
  • [9] Determination of in situ-generated dimethyldioxirane from an aqueous matrix using selected ion monitoring
    Delcomyn, CA
    MacLean, HS
    Henley, MV
    Renard, JJ
    JOURNAL OF CHROMATOGRAPHY A, 2005, 1089 (1-2) : 211 - 218
  • [10] Synthesis, crystal structures and properties of two complexes constructed from in situ-generated new ligands
    Xu, Hai-Jun
    Xu, Li
    INORGANICA CHIMICA ACTA, 2013, 394 : 140 - 145