Synthesis of (Hetero)arylated Pyridazin-3(2H)-ones via Negishi Reaction Involving Zincated Pyridazin-3(2H)-ones

被引:0
|
作者
Verhelst, Tom [1 ]
Liu, Zuming [1 ]
Maes, Jens [1 ]
Maes, Bert U. W. [1 ]
机构
[1] Univ Antwerp, Dept Chem, B-2020 Antwerp, Belgium
来源
JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 76卷 / 23期
关键词
DERIVATIVES; PD; COMPLEXES; AROMATICS; EFFICIENT; HALIDES; SYSTEMS; DESIGN;
D O I
10.1021/jo201587J
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Zincated pyridazin-3(2H)-ones generated via bromine magnesium exchange followed by transmetalation using ZnCl2 or via lactam-directed ortho C4-H zincation with TMPZnCl center dot LiCl have been synthesized. These in situ created organometalfics can be used in Negishi reactions with iodo(hetero)arenes delivering a new approach toward (hetero)arylpyridazin-3(2H)-ones.
引用
收藏
页码:9648 / 9659
页数:12
相关论文
共 50 条
  • [1] Four simple pyridazin-3(2H)-ones
    Blake, AJ
    McNab, H
    ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1996, 52 : 2622 - 2627
  • [2] Recent progress in pyridazin-3(2H)-ones chemistry
    Lee, SG
    Kim, JJ
    Kim, HK
    Kweon, DH
    Kang, YJ
    Cho, SD
    Kim, SK
    Yoon, YJ
    CURRENT ORGANIC CHEMISTRY, 2004, 8 (15) : 1463 - 1480
  • [3] Functionalization and synthetic application of pyridazin-3(2H)-ones
    Kim, SK
    Kweon, DH
    Cho, SD
    Kang, YJ
    Park, KH
    Lee, SG
    Yoon, YJ
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2005, 42 (03) : 353 - 359
  • [4] Pyridazin-3(2H)-ones: the versatile pharmacophore of medicinal significance
    Ranju Bansal
    Sridhar Thota
    Medicinal Chemistry Research, 2013, 22 : 2539 - 2552
  • [5] Pyridazin-3(2H)-ones: the versatile pharmacophore of medicinal significance
    Bansal, Ranju
    Thota, Sridhar
    MEDICINAL CHEMISTRY RESEARCH, 2013, 22 (06) : 2539 - 2552
  • [6] Efficient N-arylation of pyridazin-3(2H)-ones
    Kim, JJ
    Park, YD
    Cho, SD
    Kim, HK
    Chung, HA
    Lee, SG
    Falck, JR
    Yoon, YJ
    TETRAHEDRON LETTERS, 2004, 45 (48) : 8781 - 8784
  • [7] Synthesis of Functionalized Pyridazin-3(2H)-ones via Nucleophilic Substitution of Hydrogen (SNH)
    Verhelst, Tom
    Verbeeck, Stefan
    Ryabtsova, Oxana
    Depraetere, Stefaan
    Maes, Bert U. W.
    ORGANIC LETTERS, 2011, 13 (02) : 272 - 275
  • [8] Synthesis of Functionalized Pyridazin-3(2H)-ones via Bromine-Magnesium Exchange on Bromopyridazin-3(2H)-ones
    Ryabtsova, Oxana
    Verhelst, Tom
    Baeten, Mattijs
    Velde, Christophe M. L. Vande
    Maes, Bert U. W.
    JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (24): : 9440 - 9445
  • [9] SYNTHESIS OF 6-(ALPHA-STYRYL)PYRIDAZIN-3(2H)-ONES
    ISMAIL, MF
    SHAMS, NA
    MOSTAFA, OE
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1982, 21 (04): : 371 - 372
  • [10] Reactivity of pyridazin-3(2H) thiones
    Kandile, NG
    Zaky, HT
    Mohamed, MI
    Elgazwy, ASSH
    HETEROATOM CHEMISTRY, 2003, 14 (04) : 334 - 341