Metal-Free Synthesis of Benzo[a]phenanthridines from Aromatic Aldehydes, Cyclohexanones, and Aromatic Amines

被引:19
|
作者
Jiang, Pingyu [1 ]
Shan, Zhifei [1 ]
Chen, Shanping [1 ]
Wang, Quanyuan [1 ]
Jiang, Shuxin [1 ]
Zheng, Haolin [1 ]
Deng, Guo-Jun [1 ,2 ]
机构
[1] Xiangtan Univ, Key Lab Green Organ Synth & Applicat Hunan Prov, Key Lab Environmentally Friendly Chem & Applicat, Minist Educ,Coll Chem, Xiangtan 411105, Hunan, Peoples R China
[2] South China Univ Technol, Guangdong Prov Key Lab Luminescence Mol Aggregate, Guangzhou 510640, Guangdong, Peoples R China
来源
CHINESE JOURNAL OF CHEMISTRY | 2022年 / 40卷 / 03期
基金
中国国家自然科学基金;
关键词
Nitrogen heterocycles; Multicomponent reactions; Dehydroaromatization; Cyclization; Metal-free; BENZOPHENANTHRIDINE ALKALOIDS; 3-COMPONENT REACTION; PHENANTHRIDINES; DERIVATIVES; QUINOLINES; CYCLIZATION; ANNULATION; ARYLATION; PYRIDINES;
D O I
10.1002/cjoc.202100670
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Comprehensive Summary A three-component synthesis of benzo[alpha]phenanthridines from aromatic aldehydes, cyclohexanones, and aromatic amines has been developed, which is mediated by KI/DMSO/camphorsulfonic acid to afford a variety of functionalized benzo[alpha]phenanthridines in satisfactory yields. The present strategy provides a biaryl motif ortho to the nitrogen atom which has the potential to be used as ligand by further modification. With the advantages of readily available starting materials, transition-metal-free conditions, gram-scale synthesis, and broad substrate scope, this three-component protocol provides an efficient approach for the preparation of diverse benzo[alpha]phenanthridines.
引用
收藏
页码:365 / 370
页数:6
相关论文
共 50 条
  • [21] Metal-Free Synthesis of Homopropargylic Alcohols from Aldehydes
    Teodoro, Bruno V. M.
    Silva, Luiz F., Jr.
    JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (22): : 11787 - 11791
  • [22] Continuous-flow synthesis of primary amines: Metal-free reduction of aliphatic and aromatic nitro derivatives with trichlorosilane
    Porta, Riccardo
    Puglisi, Alessandra
    Colombo, Giacomo
    Rossi, Sergio
    Benaglia, Maurizio
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2016, 12 : 2614 - 2619
  • [23] Metal-Free Synthesis of Secondary Arylamines: An Aliphatic-to-Aromatic Transformation
    Teresa Barros, M.
    Dey, Suvendu S.
    Maycock, Christopher D.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (04) : 742 - 747
  • [24] Metal-free synthesis of amides by oxidative amidation of aldehydes with amines in PEG/oxidant system
    Liang, Jun
    Lv, Jing
    Shang, Zhi-cai
    TETRAHEDRON, 2011, 67 (44) : 8532 - 8535
  • [25] The Mannich reaction of dialkyl ketones, aromatic aldehydes and aromatic amines
    Zou, JH
    ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1996, 28 (05) : 618 - 622
  • [26] Synthesis of Aromatic Sulfones from SO2 and Organosilanes Under Metal-free Conditions
    von Wolff, Niklas
    Char, Joelle
    Frogneux, Xavier
    Cantat, Thibault
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (20) : 5616 - 5619
  • [27] Metal-Free Synthesis of 1,3-Dioxane Derivatives from Aromatic Alkynes and Paraformaldehyde
    Hu, Xin
    Ding, Man-Hua
    Zeng, Fei
    SYNLETT, 2022, 33 (10) : 959 - 964
  • [28] O-Doped Carbon Nitride: A Recyclable, Metal-free Photocatalyst for Oxidative Amidation of Aromatic Aldehydes and Amines under Visible Light Irradiation
    Huang, Zezhao
    Xu, Hang
    Zhang, Wenjie
    Liang, Zeyao
    Lin, Ping
    Zhu, Li
    Yao, Xiaoquan
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2025,
  • [29] THE SYNTHESIS OF AROMATIC ALDEHYDES
    FERGUSON, LN
    CHEMICAL REVIEWS, 1946, 38 (02) : 227 - 254
  • [30] THE MANNICH REACTION BETWEEN AROMATIC KETONES, AROMATIC-ALDEHYDES AND AROMATIC-AMINES
    YI, L
    LEI, HS
    ZOU, JH
    XU, XJ
    SYNTHESIS-STUTTGART, 1991, (09): : 717 - 718