Synthesis of 2,4,6-Trisubstituted Pyridines by Oxidative Eosin Y Photoredox Catalysis

被引:70
|
作者
Rohokale, Rajendra S. [1 ]
Koenig, Burkhard [2 ]
Dhavale, Dilip D. [1 ]
机构
[1] Savitribai Phule Pune Univ, Garware Res Ctr, Dept Chem, Pune 411007, Maharashtra, India
[2] Univ Regensburg, Inst Organ Chem, Univ Str 31, D-93053 Regensburg, Germany
来源
JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 81卷 / 16期
关键词
SOLVENT-FREE REACTION; ARYL DIAZONIUM SALTS; METAL-FREE; SUBSTITUTED PYRIDINES; EFFICIENT SYNTHESIS; 2,4,6-TRIARYLPYRIDINES; NITROGEN; LIGANDS; FUNCTIONALIZATION; ARYLATION;
D O I
10.1021/acs.joc.6b00979
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Eosin Y, an organic dye, was activated as a photoredox catalyst in the presence of molecular oxygen using visible light and, when it was used in the reaction of aryl ketones and benzyl amines, afforded good yields (52-87%) of 2,4,6-triarylpyridines (21 examples) at ambient temperature. The aryl groups at the 2- and 6-positions are derived from ketones, while benzyl, amine plays the dual role of providing an aryl functionality at the 4-position of pyridine as well as being a nitrogen donor.
引用
收藏
页码:7121 / 7126
页数:6
相关论文
共 50 条
  • [1] Solid-phase synthesis of 2,4,6-trisubstituted pyridines
    Chiu, CF
    Tang, ZL
    Ellingboe, JW
    JOURNAL OF COMBINATORIAL CHEMISTRY, 1999, 1 (01): : 73 - 77
  • [2] 2,4,6-TRISUBSTITUTED PYRIDINES - SYNTHESIS, FLUORESCENCE, AND SCINTILLATOR PROPERTIES
    BARRIO, MDCG
    BARRIO, JR
    WALKER, G
    NOVELLI, A
    LEONARD, NJ
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (15) : 4891 - 4895
  • [3] STUDIES ON CYCLOIMMONIUM YLIDS - SYNTHESIS OF SOME NEW 2,4,6-TRISUBSTITUTED PYRIDINES
    TEWARI, RS
    NAGPAL, DK
    CHATURVEDI, SC
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1979, 17 (06): : 569 - 571
  • [4] STUDIES ON CYCLOIMMONIUM YLIDES - SYNTHESIS OF SOME NEW 2,4,6-TRISUBSTITUTED PYRIDINES .2.
    TEWARI, RS
    CHATURVEDI, SC
    NAGPAL, DK
    JOURNAL OF CHEMICAL AND ENGINEERING DATA, 1980, 25 (03): : 293 - 295
  • [5] An Orthogonal Synthetic Approach to Nonsymmetrical Bisazolyl 2,4,6-Trisubstituted Pyridines
    Gamonal Ruiz-Crespo, Arturo
    Galan-Fernandez, Laura
    Martinez-Martin, Paloma
    Rodriguez-Ubis, Juan Carlos
    MOLECULES, 2022, 27 (05):
  • [6] Design, synthesis, characterization, photophysical and pH chemosensor studies of novel 2,4,6-trisubstituted pyridines
    Naik, Nirmala S.
    Bhat, Navya S.
    Hegde, Arpana G.
    Bhat, Swati S.
    Kirasur, Akshay
    Patil, Anilkumar
    Shastri, Lokesh A.
    Sunagar, Vinay
    SYNTHETIC COMMUNICATIONS, 2018, 48 (05) : 511 - 523
  • [7] Synthesis and in vitro anticancer evaluation of novel 2,4,6-trisubstituted pyridines designed as AKT inhibitors
    Miguel, Jorge
    Hernandez Campos, Alicia
    Castillo-Bocanegra, Rafael
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2019, 258
  • [8] Synthesis of 2,4,6-trisubstituted pyrimidines as antimalarial agents
    Agarwal, A
    Srivastava, K
    Puri, SK
    Chauhan, PMS
    BIOORGANIC & MEDICINAL CHEMISTRY, 2005, 13 (15) : 4645 - 4650
  • [9] Synthesis of 2,4,6-trisubstituted pyridines using palladium-catalyzed cross-coupling reaction
    Trejo, Pedro
    Hernandez Campos, Alicia
    Castillo-Bocanegra, Rafael
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2015, 250
  • [10] STERICALLY HINDERED BASES - SYNTHESIS OF 2,4,6-TRISUBSTITUTED PYRIMIDINES
    MARTINEZ, AG
    FERNANDEZ, AH
    ALVAREZ, RM
    LOSADA, MCS
    VILCHEZ, DM
    SUBRAMANIAN, LR
    HANACK, M
    SYNTHESIS-STUTTGART, 1990, (10): : 881 - 882