One-pot synthesis of 2,6-diaryl-4,5-dihydropyridazin-3(2H)-ones: Copper catalyzed annulation of aldehydes, arylhydrazines and 3-acryloyloxazolidin-2-one

被引:0
|
作者
Zhao, Jianbo
Lei, Shengshu
Wu, Min
Pang, Can
Li, Hao [1 ]
机构
[1] East China Univ Sci & Technol, State Key Lab Bioengn Reactor, Shanghai Key Lab New Drug Design, 130 Mei long Rd, Shanghai 200237, Peoples R China
关键词
Annulation; Copper; One; -pot; Pyridazinones; PROGESTERONE-RECEPTOR LIGANDS; BIOLOGICAL EVALUATION; PHTHALAZINONE DERIVATIVES; CARDIOTONIC AGENTS; PYRIDAZINONE; 4,5-DIHYDRO-3(2H)-PYRIDAZINONES; SELECTIVITY; AFFINITY; SERIES;
D O I
10.1016/j.tetlet.2023.154473
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The three-component synthesis of pyridazinones from aldehydes, arylhydrazines and 3-acryloyloxazo-lidin-2-one catalyzed by Cu(OTf)2 has been developed. This strategy exhibits high tolerance towards many functional groups including various aliphatic, aromatic and hetero-aromatic aldehydes to give 2,6-diaryl-4,5-dihydropyridazin-3(2H)-one products in moderate to high yields.(c) 2023 Elsevier Ltd. All rights reserved.
引用
收藏
页数:4
相关论文
共 50 条
  • [1] ONE-POT SYNTHESIS OF NOVEL 2-(THIAZOL-2-YL)-4,5-DIHYDROPYRIDAZIN-3(2H)-ONE DERIVATIVES CATALYZED BY ACTIVATED KSF
    Mahmoodi, Nosrat O.
    Safari, Niloufar
    Sharifzadeh, Bahman
    SYNTHETIC COMMUNICATIONS, 2014, 44 (02) : 245 - 250
  • [2] 6-Phenyl-4,5-dihydropyridazin-3(2H)-one
    Abourichaa, S
    Benchat, N
    Anaflous, A
    Melhaoui, A
    Ben-Hadda, T
    Oussaid, B
    El Bali, B
    Bolte, M
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2003, 59 : O802 - O803
  • [3] PREPARATION AND SOME REACTIONS OF 4-ARYL-4,5-DIHYDROPYRIDAZIN-3(2H)-ONES AND 5-ARYL-4,5-DIHYDROPYRIDAZIN-3(2H)-ONES
    BREUKELMAN, SP
    MEAKINS, GD
    ROE, AM
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (08): : 1627 - 1635
  • [4] 6-Methyl-2-phenyl-4,5-dihydropyridazin-3(2H)-one
    Sekkak, Hanan
    Rakib, El Mostapha
    Zouihri, Hafid
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2011, 67 : O1709 - U879
  • [5] SiO2-BiCl3 as Heterogeneous Catalyzed Synthesis of 6-Methyl-2-aryl-4,5-dihydropyridazin-3(2H)-one Derivatives
    Hote, Baliram S.
    Sawant, Ajay S.
    Sawant, Sanjay S.
    POLYCYCLIC AROMATIC COMPOUNDS, 2020, 40 (05) : 1501 - 1509
  • [6] THE BEHAVIOR OF 4,5-DIHYDROPYRIDAZIN-3(2H)-ONE DERIVATIVES TOWARDS ORGANOMETALLIC COMPOUNDS
    FATEEN, AK
    ISMAIL, MF
    KADDAH, AM
    SHAMS, NA
    JOURNAL FUR PRAKTISCHE CHEMIE, 1980, 322 (04): : 617 - 622
  • [7] Synthesis and evaluation of 2-substituted-6-phenyl-4,5-dihydropyridazin-3(2H)-ones as potent inodilators
    Kumar, Dinesh
    Carron, Rosalia
    De la Calle, Carmen
    Jindal, Dharam Paul
    Bansal, Ranju
    ACTA PHARMACEUTICA, 2008, 58 (04) : 393 - 405
  • [8] A convenient synthesis of new phosphonomethyl-containing 4,5-dihydropyridazin-3(2H)-ones
    Bejaoui, Oumayma
    Abdelli, Abderrahmen
    M'rabet, Hedi
    Moreau, Xavier
    Efrit, Mohamed Lotfi
    Prim, Damien
    MENDELEEV COMMUNICATIONS, 2023, 33 (05) : 640 - 641
  • [9] [4+2] Annulation Reaction of In Situ Generated Azoalkenes with Azlactones: Access to 4,5-Dihydropyridazin-3(2H)-Ones
    Yuan, Wei-Cheng
    Quan, Bao-Xue
    Zhao, Jian-Qiang
    You, Yong
    Wang, Zhen-Hua
    Zhou, Ming-Qiang
    JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (18): : 11812 - 11821
  • [10] NOVEL ONE-POT SYNTHESIS FOR 2,5-DIARYL AND 5-ARYL-PYRIDAZIN-3(2H)-ONES
    Basanagouda, Mahantesha
    Kulkarni, Manohar V.
    SYNTHETIC COMMUNICATIONS, 2011, 41 (17) : 2569 - 2582