Chemoselective N- and O-Difluoromethylation of 2-Pyridones, Isoquinolinones, and Quinolinones with TMSCF2Br

被引：21
作者：
Zhu, Ziyue [1 ,2 ]
Krishnamurti, Vinayak [1 ,2 ]
Ispizua-Rodriguez, Xanath [1 ,2 ]
Barrett, Colby [1 ,2 ]
Prakash, G. K. Surya [1 ,2 ]
机构：
[1] Univ Southern Calif, Loker Hydrocarbon Res Inst, Los Angeles, CA 90089 USA
[2] Univ Southern Calif, Dept Chem, Los Angeles, CA 90089 USA
来源：
ORGANIC LETTERS | 2021年 / 23卷 / 16期
关键词：
NUCLEOPHILIC DIFLUOROMETHYLATION; DIFLUOROCARBENE; REAGENT; POTENT;
D O I：
10.1021/acs.orglett.1c02305
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An operationally simple protocol for direct N- and O-difluoromethylation of 2-pyridones, quinolinones, and isoquinolinones using commercially available TMSCF2Br is disclosed. The chemoselectivity is modulated by simple variations in temperature, solvent, and strength of the base. Diverse, synthetically relevant functional groups are tolerated, including functional groups that have reported reactivity with TMSCF2Br. Gram-scale reactions to prepare both N- and O-difluoromethyl compounds are included.
引用
收藏
页码：6494 / 6498
页数：5
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共 44 条
  • [1] Fluoride based electrode materials for advanced energy storage devices
    Amatucci, Glenn G.
    Pereira, Nathalie
    [J]. JOURNAL OF FLUORINE CHEMISTRY, 2007, 128 (04) : 243 - 262
  • [2] Facile one-pot synthesis of N-difluoromethyl-2-pyridone derivatives
    Ando, Makoto
    Wada, Toshihiro
    Sato, Nagaaki
    [J]. ORGANIC LETTERS, 2006, 8 (17) : 3805 - 3808
  • [3] Discovery of pyridone-containing imidazolines as potent and selective inhibitors of neuropeptide Y Y5 receptor
    Ando, Makoto
    Sato, Nagaaki
    Nagase, Tsuyoshi
    Nagai, Keita
    Ishikawa, Shiho
    Takahashi, Hirobumi
    Ohtake, Norikazu
    Ito, Junko
    Hirayama, Mioko
    Mitobe, Yuko
    Iwaasa, Hisashi
    Gomori, Akira
    Matsushita, Hiroko
    Tadano, Kiyoshi
    Fujino, Naoko
    Tanaka, Sachiko
    Ohe, Tomoyuki
    Ishihara, Akane
    Kanatani, Akio
    Fukami, Takehiro
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2009, 17 (16) : 6106 - 6122
  • [4] One-pot preparation of (RSe)2CF2 and (RS)2CF2 compounds via insertion of TMSCF3-derived difluorocarbene into diselenides and disulfides
    Barrett, Colby
    Krishnamurti, Vinayak
    Oliveira, Artur Pratas
    Prakash, G. K. Surya
    [J]. TETRAHEDRON, 2019, 75 (31) : 4167 - 4173
  • [5] Organic fluorine compounds: a great opportunity for enhanced materials properties
    Berger, Ricarda
    Resnati, Giuseppe
    Metrangolo, Pierangelo
    Weber, Edwin
    Hulliger, Juerg
    [J]. CHEMICAL SOCIETY REVIEWS, 2011, 40 (07) : 3496 - 3508
  • [6] FLUORIDATED ELEMENTORGANIKA .20. SYNTHESIS OF FLUORMETHYLTRIMETHYLSILANES
    BROICHER, V
    GEFFKEN, D
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1990, 381 (03) : 315 - 320
  • [7] Visible-Light- and Oxygen-Promoted Direct Csp2-H Radical Difluoromethylation of Coumarins and Antifungal Activities
    Dai, Peng
    Yu, Xiang
    Teng, Peng
    Zhang, Wei-Hua
    Deng, Chao
    [J]. ORGANIC LETTERS, 2018, 20 (21) : 6901 - 6905
  • [8] Direct Nucleophilic Difluoromethylation of Carbonyl Compounds
    Deng, Zuyong
    Lin, Jin-Hong
    Cai, Ji
    Xiao, Ji-Chang
    [J]. ORGANIC LETTERS, 2016, 18 (13) : 3206 - 3209
  • [9] A NEW SERIES OF PYRIDINONE DERIVATIVES AS POTENT NONNUCLEOSIDE HUMAN-IMMUNODEFICIENCY-VIRUS TYPE-1 SPECIFIC REVERSE-TRANSCRIPTASE INHIBITORS
    DOLLE, V
    FAN, E
    NGUYEN, CH
    AUBERTIN, AM
    KIRN, A
    ANDREOLA, ML
    JAMIESON, G
    TARRAGOLITVAK, L
    BISAGNI, E
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1995, 38 (23) : 4679 - 4686
  • [10] Six Years (2012-2018) of Researches on Catalytic EZH2 Inhibitors: The Boom of the 2-Pyridone Compounds
    Fioravanti, Rossella
    Stazi, Giulia
    Zwergel, Clemens
    Valente, Sergio
    Mai, Antonello
    [J]. CHEMICAL RECORD, 2018, 18 (12) : 1818 - 1832
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