Ru(ii)-catalyzed oxidative coupling of sulfoxonium ylides with amines: efficient synthesis of α-ketoamides and indolo[2,1-a]isoquinolines

被引：2
作者：
Changmai, Sumi [1 ,2 ]
Gogoi, Tribeni [1 ,2 ]
Phukon, Jyotshna [1 ,2 ]
Das, Bipul [1 ,2 ]
Gogoi, Sanjib [1 ,2 ]
机构：
[1] North East Inst Sci & Technol, Chem Sci & Technol Div, Appl Organ Chem, CSIR, Jorhat 785006, India
[2] Acad Sci & Innovat Res AcSIR, Ghaziabad 201002, India
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2023年 / 21卷 / 15期
关键词：
INHIBITORS; ACCESS; AMIDATION; RECEPTOR; AMIDES; CARBON;
D O I：
10.1039/d3ob00187c
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The first use of sulfoxonium ylides for the synthesis of alpha-ketoamides is described via a Ru(ii)-catalyzed amidation reaction with amines. The same Ru(ii)-catalyzed reaction of sulfoxonium ylides with 2-phenylindoles provided indolo[2,1-a]isoquinolines instead of alpha-ketoamides.
引用
收藏
页码：3235 / 3244
页数：10
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  • [31] 3 MORE CYCLOTHEONAMIDES, CYCLOTHEONAMIDE-C, CYCLOTHEONAMIDE-D, AND CYCLOTHEONAMIDE-D, POTENT THROMBIN INHIBITORS FROM THE MARINE SPONGE THEONELLA-SWINHOEI
    NAKAO, Y
    MATSUNAGA, S
    FUSETANI, N
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 1995, 3 (08) : 1115 - 1122
  • [32] Ruthenium-catalyzed C-H Functionalization/Annulation of N-Aryl Indazoles/Phthalazines with Sulfoxonium Ylides to access Tetracyclic-fused Cinnolines
    Pan, Changduo
    Yuan, Cheng
    Yu, Jin-Tao
    [J]. ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 11 (08)
  • [33] Hydroxyl-Directed Ru(II)-Catalyzed Synthesis of Fused Dihydrofurans Using 1,4-Dioxane and Sulfoxonium Ylides as Annulating Agents
    Phukon, Jyotshna
    Bhorali, Pratiksha
    Changmai, Sumi
    Gogoi, Sanjib
    [J]. ORGANIC LETTERS, 2023, 25 (01) : 215 - 219
  • [34] Divergent Reactivity of gem-Difluoro-enolates toward Nitrogen Electrophiles: Unorthodox Nitroso Aldol Reaction for Rapid Synthesis of α-Ketoamides
    Reddy, Mallu Kesava
    Ramakrishna, Isai
    Baidya, Mahiuddin
    [J]. ORGANIC LETTERS, 2018, 20 (15) : 4610 - 4613
  • [35] Synthesis of N-Arylisatins by the Reaction of Arynes with Methyl 2-Oxo-2-(arylamino)acetates
    Rogness, Donald C.
    Larock, Richard C.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (12) : 4980 - 4986
  • [36] Visible-light initiated copper( I)-catalysed oxidative C-N coupling of anilines with terminal alkynes: one-step synthesis of α-ketoamides
    Sagadevan, Arunachalam
    Ragupathi, Ayyakkannu
    Lin, Chun-Cheng
    Hwu, Jih Ru
    Hwang, Kuo Chu
    [J]. GREEN CHEMISTRY, 2015, 17 (02) : 1113 - 1119
  • [37] Direct and Highly Enantioselective Iso-Pictet-Spengler Reactions with α-Ketoamides: Access to Underexplored Indole Core Structures
    Schoenherr, Heike
    Leighton, James L.
    [J]. ORGANIC LETTERS, 2012, 14 (10) : 2610 - 2613
  • [38] Ruthenium (II)-Catalyzed Oxidant-Free Coupling/Cyclization of Benzimidates and Sulfoxonium Ylides to Form Substituted Isoquinolines
    Shi, Xinxia
    Wang, Rongchao
    Zeng, Xiaofei
    Zhang, Yilan
    Hu, Huiling
    Xie, Chunsong
    Wang, Min
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (21) : 4049 - 4053
  • [39] α-Carbonyl sulfoxonium ylides in transition metal-catalyzed C-H activation: a safe carbene precursor and a weak directing group
    Singh, Anurag
    Kumar, Shreemoyee
    Volla, Chandra M. R.
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2023, 21 (05) : 879 - 909
  • [40] Synthesis and biological evaluation of α-ketoamides as inhibitors of the Dengue virus protease with antiviral activity in cell-culture
    Steuer, Christian
    Gege, Christian
    Fischl, Wolfgang
    Heinonen, Karl H.
    Bartenschlager, Ralf
    Klein, Christian D.
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2011, 19 (13) : 4067 - 4074
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