A novel route to 2,3-pyrazol-1(5H)-ones via palladium-catalyzed carbonylation of 1,2-diaza-1,3-butadienes

被引：64
作者：
Boeckman, RK [1 ]
Reed, JE [1 ]
Ge, P [1 ]
机构：
[1] Univ Rochester, Dept Chem, Rochester, NY 14627 USA
来源：
ORGANIC LETTERS | 2001年 / 3卷 / 23期
关键词：
D O I：
10.1021/ol016565x
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
[GRAPHICS] A novel Pd(0)-catalyzed carbonylation of both isolable 1,2-diaza-1,3-butadienes and those generated in situ by extrusion of SO2 and CO2 from heterocyclic precursors is described. The reaction proceeds at room temperature to 110 degreesC under 1-2 atm of CO to afford 2,3-pyrazol-1(5H)-ones in good to excellent yields. The effect of catalyst structure and stability on the carbonylation reaction is evaluated.
引用
收藏
页码：3651 / 3653
页数：3
相关论文
共 50 条
  • [21] First preparation and reaction of polymer-bound 1,2-diaza-1,3-butadienes. A convenient entry to 4-triphenylphosphoranylidene-4,5-dihydropyrazol-5-ones
    Attanasi, OA
    Filippone, P
    Guidi, B
    Hippe, T
    Mantellini, F
    Tietze, LF
    TETRAHEDRON LETTERS, 1999, 40 (52) : 9277 - 9280
  • [22] Palladium-catalyzed Csp2-H carbonylation of aromatic oximes: selective access to benzo[d][1,2] oxazin-1-ones and 3-methyleneisoindolin-1-ones
    Xu, Yanli
    Hu, Weigao
    Tang, Xiaodong
    Zhao, Jinwu
    Wu, Wanqing
    Jiang, Huanfeng
    CHEMICAL COMMUNICATIONS, 2015, 51 (31) : 6843 - 6846
  • [23] 1,3-Dipolar cycloaddition of azomethine imines to ethynyl hetarenes: A synthetic route to 2,3-dihydropyrazolo[1,2-a]pyrazol-1(5H)-one based heterobiaryls
    Nelina-Nemtseva, Julia I.
    Gulevskaya, Anna V.
    Suslonov, Vitaliy V.
    Misharev, Alexander D.
    TETRAHEDRON, 2018, 74 (10) : 1101 - 1109
  • [24] Palladium-Catalyzed Oxidative Carbonylation of the Alkenyl C-H Bonds of Enamides: Synthesis of 1,3-Oxazin-6-ones
    Chen, Ming
    Ren, Zhi-Hui
    Wang, Yao-Yu
    Guan, Zheng-Hui
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (52) : 14196 - 14199
  • [25] Regioselective synthesis of spiro-cyclopropanated 1-aminopyrrol-2-ones by Bi(OTf)3-catalyzed one-pot 'Mukaiyama-Michael addition/cyclization/ring-contraction' reactions of 1,2-bis(trimethylsilyloxy)cyclobutene with 1,2-diaza-1,3-butadienes
    Attanas, Orazio A.
    Favi, Gianfranco
    Giorgi, Gianluca
    Mantellini, Fabio
    Karapetyan, Vahuni
    Langer, Peter
    TETRAHEDRON, 2009, 65 (28) : 5456 - 5461
  • [26] Copper-Catalyzed Synthesis of 5-Aryl-6-(Trifluoromethyl)-2,3-Dihydropyrazolo[1,2-a]Pyrazol-1(5H)-One
    Zhang, Xinyu
    Wang, Hui
    Xie, Lili
    You, Chenhui
    Han, Xiaoyan
    Weng, Zhiqiang
    CHEMISTRY-AN ASIAN JOURNAL, 2021, 16 (18) : 2669 - 2673
  • [27] Diversity-oriented synthesis of functionalized 1-aminopyrroles by regioselective zinc chloride-catalyzed, one-pot 'Conjugate Addition/Cyclization' reactions of 1,3-bis(silyl enol ethers) with 1,2-diaza-1,3-butadienes
    Karapetyan, Vahuni
    Mkrtchyan, Satenik
    Schmidt, Andreas
    Attanasi, Orazio A.
    Favi, Gianfranco
    Mantellini, Fabio
    Villinger, Alexander
    Fischer, Christine
    Langer, Peter
    ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (09) : 1331 - 1336
  • [28] Double 1,4-addition of malonate to 1,2-diaza-1,3-butadienes: a useful route to previously unknown symmetric and unsymmetric 1,6-dioxo-2,7-diazaspiro[4.4]nona-3,8-dienes
    Attanasi, OA
    De Crescentini, L
    Filippone, P
    Mantellini, F
    NEW JOURNAL OF CHEMISTRY, 2001, 25 (04) : 534 - 537
  • [29] Synthesis of 3-substituted-3,4-dihydro-2H-1,3-benzothiazin-2-ones via a highly regioselective palladium-catalyzed carbonylation of 2-substituted-2,3-dihydro-1,2-benzisothiazoles
    Rescourio, Gwenaella
    Alper, Howard
    JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (04) : 1612 - 1615
  • [30] Enantioselective synthesis of 3,6-Dihydro-1H-pyridin-2-ones:: Unexpected regioselectivity in the palladium-catalyzed decarboxylative carbonylation of 5-vinyloxazolidin-2-ones
    Knight, JG
    Ainge, SW
    Harm, AM
    Harwood, SJ
    Maughan, HI
    Armour, DR
    Hollinshead, DM
    Jaxa-Chamiec, AA
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (12) : 2944 - 2945
12345