Ruthenium-Catalyzed Straightforward Synthesis of 1,2,3,4-Tetrahydronaphthyridines via Selective Transfer Hydrogenation of Pyridyl Ring with Alcohols

被引:49
|
作者
Xiong, Biao [1 ]
Li, Ya [1 ]
Lv, Wan [1 ]
Tan, Zhenda [1 ]
Jiang, Huanfeng [1 ]
Zhang, Min [1 ]
机构
[1] S China Univ Technol, Sch Chem & Chem Engn, Guangzhou 510641, Peoples R China
基金
中国国家自然科学基金;
关键词
H BOND FUNCTIONALIZATION; ASYMMETRIC HYDROGENATION; DEHYDROGENATIVE SYNTHESIS; N-ALKYLATION; IONIC LIQUID; AMINES; REDUCTION; COMPLEX; ACID; PHOTOSENSITIZERS;
D O I
10.1021/acs.orglett.5b01976
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Through a ruthenium-catalyzed selective hydrogen transfer coupling reaction, a novel straightforward synthesis of 1,2,3,4-tetrahydronaphthyridines from o-amino-pyridyl methanols and alcohols has been developed. The synthetic protocol proceeds in an atom- and step-economic fashion together with the advantages of operational simplicity, broad substrate scope, production of water as the only byproduct, and no need for external reducing reagents such as high pressure H-2 gas, offering a highly practical approach for accessing this type of structurally unique products.
引用
收藏
页码:4054 / 4057
页数:4
相关论文
共 50 条
  • [1] Ruthenium-Catalyzed Direct Synthesis of Semisaturated Bicyclic. Pyrimidines via Selective Transfer Hydrogenation
    Xiong, Biao
    Jiang, Jingxing
    Zhang, Shudi
    Jiang, Huanfeng
    Ke, Zhuofeng
    Zhang, Min
    ORGANIC LETTERS, 2017, 19 (10) : 2730 - 2733
  • [2] Convenient Synthesis of Quinolines from α-2-Nitroaryl Alcohols and Alcohols via a Ruthenium-catalyzed Hydrogen Transfer Strategy
    Xie, Feng
    Zhang, Min
    Chen, Mengmeng
    Lv, Wan
    Jiang, Huanfeng
    CHEMCATCHEM, 2015, 7 (02) : 349 - 353
  • [3] Stereodivergent Access to Enantioenriched Epoxy Alcohols with Three Stereogenic Centers via Ruthenium-Catalyzed Transfer Hydrogenation
    Zhao, Zhifei
    Bagdi, Prasanta Ray
    Yang, Shuang
    Liu, Jinggong
    Xu, Weici
    Fang, Xinqiang
    ORGANIC LETTERS, 2019, 21 (14) : 5491 - 5494
  • [4] Synthesis of pyrroles via ruthenium-catalyzed nitrogen-transfer [2
    Matsui, Kazuma
    Shibuya, Masatoshi
    Yamamoto, Yoshihiko
    COMMUNICATIONS CHEMISTRY, 2018, 1
  • [5] Ruthenium-Catalyzed Highly Enantioselective Synthesis of cis-3-Quinuclidinols via DKR Asymmetric Transfer Hydrogenation
    Luo, Zhonghua
    Wang, Zhongqing
    Sun, Guodong
    Jian, Weilin
    Jiang, Fengkai
    Luan, Baolei
    Li, Ridong
    Zhang, Lei
    ORGANIC LETTERS, 2020, 22 (11) : 4322 - 4326
  • [6] Enantioselective Synthesis of 2-Hydroxyalkyl Diarylphosphinates by Ruthenium-Catalyzed Asymmetric Transfer Hydrogenation
    Zhang, Kaili
    Yang, Yuping
    Liu, Huan
    Liu, Qixing
    Lv, Jinliang
    Zhou, Haifeng
    ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (17) : 4106 - 4110
  • [7] Enantioselective Synthesis of Chiral β-Aryloxy Alcohols by Ruthenium-Catalyzed Ketone Hydrogenation via Dynamic Kinetic Resolution (DKR)
    Bai, Wen-Ju
    Xie, Jian-Hua
    Li, Ya-Li
    Liu, Sheng
    Zhou, Qi-Lin
    ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (01) : 81 - 84
  • [8] Diastereoselective synthesis of syn-3,5-dihydroxyesters via ruthenium-catalyzed asymmetric transfer hydrogenation
    Everaere, K
    Franceschini, N
    Mortreux, A
    Carpentier, JF
    TETRAHEDRON LETTERS, 2002, 43 (14) : 2569 - 2571
  • [9] 2-azanorbornyl alcohols: Very efficient ligands for ruthenium-catalyzed asymmetric transfer hydrogenation of aromatic ketones
    Alonso, DA
    Nordin, SJM
    Roth, P
    Tarnai, T
    Andersson, PG
    Thommen, M
    Pittelkow, U
    JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (10): : 3116 - 3122
  • [10] Ruthenium-catalyzed dynamic kinetic asymmetric transfer hydrogenation: stereoselective access to syn 2-(1,2,3,4-tetrahydro-1-isoquinolyl)ethanol derivatives
    Zheng, Long-Sheng
    Phansavath, Phannarath
    Ratovelomanana-Vidal, Virginie
    ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (08): : 1366 - 1370