Practical Pd(TFA)2-Catalyzed Aerobic [4+1] Annulation for the Synthesis of Pyrroles via "One-Pot" Cascade Reactions

被引:3
|
作者
Yu, Yang [1 ,2 ]
Mang, Zhiguo [1 ,2 ]
Yang, Wei [3 ]
Li, Hao [1 ,2 ]
Wang, Wei [1 ,2 ,4 ]
机构
[1] East China Univ Sci & Technol, Shanghai Key Lab New Drug Design, State Key Lab Bioengn Reactor, 130 Mei Long Rd, Shanghai 200237, Peoples R China
[2] East China Univ Sci & Technol, Sch Pharm, 130 Mei Long Rd, Shanghai 200237, Peoples R China
[3] Shanghai Inst Mat Med, Shanghai 201203, Peoples R China
[4] Univ New Mexico, Dept Chem & Chem Biol, Albuquerque, NM 87131 USA
来源
CATALYSTS | 2016年 / 6卷 / 11期
基金
美国国家科学基金会;
关键词
Pd(TFA)(2); 4+1] annulation; alpha-alkenyl-dicarbonyl compounds; unprotected primary amines; one-pot; tandem reaction; regio-selective; N BOND FORMATION; WACKER-TYPE CYCLIZATION; C-H AMIDATION; ATORVASTATIN CALCIUM; SUBSTITUTED PYRROLES; OXIDATIVE AMINATION; EFFICIENT SYNTHESIS; 3+2 CYCLOADDITION; DERIVATIVES; ALKENES;
D O I
10.3390/catal6110169
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
The Pd(TFA)(2)-catalyzed [4+1] annulation of chained or cyclic alpha-alkenyl-dicarbonyl compounds and unprotected primary amines for "one-pot" synthesis of pyrroles is reported here. Enamination and amino-alkene were involved in this practical and efficient tandem reaction. The annulation products were isolated in moderate to excellent yields with O-2 as the terminal oxidant under mild conditions. In addition, this method was applied to synthesize highly regioselective aminomethylated and di(1H-pyrrol-3-yl) methane products.
引用
收藏
页数:11
相关论文
共 50 条
  • [41] One-Pot Synthesis of Pyrrolo[1,2-a]quinoxaline Derivatives through Copper-Catalyzed Cascade Reactions
    Jiang, Zengqiang
    Zhang, Jie
    Tong, Yao
    Shi, Xuesong
    Miao, Dazhuang
    Han, Shiqing
    [J]. CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2014, 34 (09) : 1845 - 1850
  • [42] Highly diastereroselective synthesis of dihydrofurans and dihydropyrroles via pyridine catalyzed formal [4+1] annulation
    Liu, Chun-Rong
    Zhu, Ben-Hu
    Zheng, Jun-Cheng
    Sun, Xiu-Li
    Xie, Zuowei
    Tang, Yong
    [J]. CHEMICAL COMMUNICATIONS, 2011, 47 (04) : 1342 - 1344
  • [43] Synthesis of pentasubstituted 2-aryl pyrroles from boryl and stannyl alkynes via one-pot sequential Ti-catalyzed [2+2+1] pyrrole synthesis/cross coupling reactions
    Cheng, Yukun
    Klein, Channing K.
    Tonks, Ian A.
    [J]. CHEMICAL SCIENCE, 2020, 11 (37) : 10236 - 10242
  • [44] One-pot synthesis of 4-methylisoquinolines via a sequential Pd-catalyzed Heck reaction and intramolecular cyclization
    Tian, Yulin
    Qi, Jianguo
    Sun, Chenbin
    Yin, Dali
    Wang, Xiaojian
    Xiao, Qiong
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (42) : 7262 - 7266
  • [45] Ultrasound Assisted and SO 4-2 /SnO 2-Catalyzed One-Pot Multicomponent Reaction for the Synthesis of 1,2,3,4,6-Pentasubstituted Piperidines
    Koduri, Ramesh Goud
    Varala, Ravi
    Boodida, Sathyanarayana
    Pagadala, Ramakanth
    Damera, Thirupathi
    [J]. INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY, 2024, 34 (02)
  • [46] One-pot two-step synthesis of 3-iodo-4-aryloxy coumarins and their Pd/C-catalyzed annulation to coumestans
    Panda, Niranjan
    Mattan, Irshad
    [J]. RSC ADVANCES, 2018, 8 (14): : 7716 - 7725
  • [47] Synthesis of multifunctional polymer containing Ni-Pd NPs via thiol-ene reaction for one-pot cascade reactions
    Kalbasi, Roozbeh Javad
    Mesgarsaravi, Niloofar
    Gharibi, Reza
    [J]. APPLIED ORGANOMETALLIC CHEMISTRY, 2019, 33 (04)
  • [48] Anticancer agent synthesis designed by artificial intelligence: Pd(OAc)2-catalyzed one-pot preparation of biphenyls and its application to a concise synthesis of various diazofluorenes
    Takabatake, Tetsuhiko
    Tomita, Hiroki
    Okada, Syo
    Hayashi, Natsumi
    Masuko, Takashi
    Toyota, Masahiro
    [J]. TETRAHEDRON LETTERS, 2020, 61 (38)
  • [49] Synthesis of substituted quinoline via copper-catalyzed one-pot cascade reactions of 2-bromobenzaldehydes with aryl methyl ketones and aqueous ammonia
    Li, Bin
    Guo, Chenhao
    Fan, Xuesen
    Zhang, Ju
    Zhang, Xinying
    [J]. TETRAHEDRON LETTERS, 2014, 55 (43) : 5944 - 5948
  • [50] One-Pot Synthesis of Substituted Furans Using Cu(OTf)2-Catalyzed Propargylation/Cycloisomerization Tandem Reaction
    Pan, Ying-ming
    Zhao, Su-yan
    Ji, Wen-hua
    Zhan, Zhuang-ping
    [J]. JOURNAL OF COMBINATORIAL CHEMISTRY, 2009, 11 (01): : 103 - 109