Intra-Intermolecular Palladium-Catalyzed Domino Reactions of Glycine Allylamides for the Synthesis of Diversely Functionalized Piperazinones

被引:22
|
作者
Broggini, Gianluigi [1 ]
Beccalli, Egle M. [2 ]
Borelli, Tea [1 ]
Brusa, Filippo [1 ]
Gazzola, Silvia [1 ]
Mazza, Alberto [2 ]
机构
[1] Univ Insubria, Dipartimento Sci & Alta Tecnol, I-22100 Como, Italy
[2] Univ Milan, DISMAB, Sez Chim Organ A Marchesini, I-20133 Milan, Italy
关键词
Homogeneous catalysis; Palladium; Domino reactions; Amination; Nitrogen heterocycles; B1 RECEPTOR ANTAGONISTS; INTRAMOLECULAR DIAMINATION; C-H; ALKENES; CYCLIZATION; POTENT; ACID; INHIBITORS; DISCOVERY; ESTERS;
D O I
10.1002/ejoc.201500386
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Easily accessible N-tosylglycine allylamides have been converted into diversely functionalized piperazinone derivatives by inter-intramolecular oxidative domino palladium-catalyzed reactions. Aminochlorination and aminoacetoxylation processes were achieved by employing CuCl2 and PhI(OAc)(2) as the oxidizing agents to give 5-chloromethyl- and 5-acetoxymethyl-substituted piperazinones, respectively.
引用
收藏
页码:4261 / 4268
页数:8
相关论文
共 50 条
  • [1] Domino Palladium-Catalyzed Heck-Intermolecular Direct Arylation Reactions
    Rene, Olivier
    Lapointe, David
    Fagnou, Keith
    ORGANIC LETTERS, 2009, 11 (20) : 4560 - 4563
  • [2] Synthesis of functionalized alkynes via palladium-catalyzed Sonogashira reactions
    Ibrahim, Mansur B.
    El Ali, Bassam
    Malik, Imran
    Fettouhi, Mohammed
    TETRAHEDRON LETTERS, 2016, 57 (05) : 554 - 558
  • [3] Palladium-Catalyzed Domino Heck/C-H Activation/Intermolecular Direct Arylation Reactions
    Lu, Zhiyao
    Cui, Yuxin
    Jia, Yanxing
    SYNTHESIS-STUTTGART, 2011, (16): : 2595 - 2599
  • [4] Palladium-catalyzed domino intramolecular N-arylation/intermolecular C-C bond formation for the synthesis of functionalized benzodiazepinediones
    Salcedo, Angela
    Neuville, Luc
    Rondot, Christophe
    Retailleau, Pascal
    Zhu, Jieping
    ORGANIC LETTERS, 2008, 10 (05) : 857 - 860
  • [5] Stereoselective synthesis of 3-alkylideneoxindoles via palladium-catalyzed domino reactions
    Yanada, R
    Obika, S
    Inokuma, T
    Yanada, K
    Yamashita, M
    Ohta, S
    Takemoto, Y
    JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (17): : 6972 - 6975
  • [6] Palladium-catalyzed domino carbonylative cyclization to access functionalized heterocycles
    Wang, Jian-Shu
    Zhang, Jiangjie
    Wang, Siqi
    Ying, Jun
    Li, Chuan-Ying
    Wu, Xiao-Feng
    Journal of Catalysis, 2022, 414 : 313 - 318
  • [7] Palladium-catalyzed domino carbonylative cyclization to access functionalized heterocycles
    Wang, Jian-Shu
    Zhang, Jiangjie
    Wang, Siqi
    Ying, Jun
    Li, Chuan-Ying
    Wu, Xiao-Feng
    JOURNAL OF CATALYSIS, 2022, 414 : 313 - 318
  • [8] A Palladium-Catalyzed Domino Reaction as Key Step for the Synthesis of Functionalized Aromatic Amino Acids
    Stark, Tina
    Suhartono, Marcel
    Goebel, Michael W.
    Lautens, Mark
    SYNLETT, 2013, 24 (20) : 2730 - 2734
  • [9] Intermolecular palladium-catalyzed aerobic oxidative amination of functionalized alkenes
    Rogers, Michelle M.
    Kotov, Vasily
    Chatwichien, Jaruwan
    Stahl, Shannon S.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2007, 233
  • [10] A Palladium-Catalyzed Domino Procedure for the Synthesis of Unsymmetrical Ureas
    Chen, Bo
    Peng, Jin-Bao
    Ying, Jun
    Qi, Xinxin
    Wu, Xiao-Feng
    ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (15) : 2820 - 2824