Synthesis of Pyrrolo[2,1,5-cd]indolizine Rings via Visible-Light-Induced Intermolecular [3+2] Cycloaddition of Indolizines and Alkynes

被引:34
作者
Zhang, Yu [1 ]
Yu, Yue [1 ]
Liang, Bing-bing [1 ]
Pei, Yong-yan [1 ]
Liu, Xiang [1 ]
Yao, Hua-gang [1 ]
Cao, Hua [1 ]
机构
[1] Guangdong Pharmaceut Univ, Sch Chem & Chem Engn, Zhongshan 528458, Peoples R China
关键词
FUNCTIONALIZATION; CONSTRUCTION; DERIVATIVES; CYCLIZATION; ARYLATION; ESTERS;
D O I
10.1021/acs.joc.0c01253
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A range of indolizine smoothly underwent visible-light-induced intermolecular [3+2] annulations with internal alkynes to afford pyrrolo[2,1,5-cd]indolizine in good to excellent yields with high regioselectivity. Through this cascade reaction, a series of fluoroactive fused indolizines with a large pi-system were conveniently synthesized. The usage of visible light as energy source with air as a stoichiometric oxidant under simple conditions makes this process attractive and practical.
引用
收藏
页码:10719 / 10727
页数:9
相关论文
共 44 条
  • [11] A simple pH fluorescent probe based on new fluorophore indolizine for imaging of living cells
    Ge, Yanqing
    Liu, Aikun
    Dong, Jian
    Duan, Guiyun
    Cao, Xiaoqun
    Li, Fuyou
    [J]. SENSORS AND ACTUATORS B-CHEMICAL, 2017, 247 : 46 - 52
  • [12] Development of a 2-methoxyphenyl-4,5-dicarbmethoxy-cycl[3.2.2] azine fluorescen sensor for Co2+
    Gopal, M. Sheela
    Anitha, I.
    Jesny, S.
    Menon, Shalini
    [J]. JOURNAL OF LUMINESCENCE, 2016, 179 : 361 - 365
  • [13] Synthetic applications of eosin Y in photoredox catalysis
    Hari, Durga Prasad
    Koenig, Burkhard
    [J]. CHEMICAL COMMUNICATIONS, 2014, 50 (51) : 6688 - 6699
  • [14] Synthesis of Pyrrolo[2,1,5-cd]indolizines through Dehydrogenative Heck Annelation of Indolizines with Diaryl Acetylenes Using Dioxygen as an Oxidant
    Hu, Huayou
    Li, Guodong
    Hu, Weiming
    Liu, Yun
    Wang, Xiang
    Kan, Yuhe
    Ji, Min
    [J]. ORGANIC LETTERS, 2015, 17 (05) : 1114 - 1117
  • [15] Synthesis and estrogen receptor binding affinities of novel pyrrolo[2,1,5-cd]indolizine derivatives
    Jorgensen, AS
    Jacobsen, P
    Christiansen, LB
    Bury, PS
    Kanstrup, A
    Thorpe, SM
    Nærum, L
    Wassermann, K
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2000, 10 (20) : 2383 - 2386
  • [16] Synthesis and pharmacology of a novel pyrrolo[2,1,5-cd] indolizine (NNC 45-0095), a high affinity non-steroidal agonist for the estrogen receptor
    Jorgensen, AS
    Jacobsen, P
    Christiansen, LB
    Bury, PS
    Kanstrup, A
    Thorpe, SM
    Bain, S
    Nærum, L
    Wassermann, K
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2000, 10 (04) : 399 - 402
  • [17] Visible Light Photocatalyzed Direct Conversion of Aryl-/Heteroarylamines to Selenides at Room Temperature
    Kundu, Debasish
    Ahammed, Sabir
    Ranu, Brindaban C.
    [J]. ORGANIC LETTERS, 2014, 16 (06) : 1814 - 1817
  • [18] STRUCTURAL-ANALYSIS OF 5-HT(3) RECEPTOR ANTAGONISTS - SYNTHESIS AND PHARMACOLOGICAL ACTIVITY OF VARIOUS AROMATIC ESTERS OR AMIDES DERIVED FROM TROPANE AND 1,2,6-TRISUBSTITUTED PIPERIDINE
    LANGLOIS, M
    SOULIER, JL
    YANG, D
    BREMONT, B
    FLORAC, C
    RAMPILLON, V
    GIUDICE, A
    [J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1993, 28 (11) : 869 - 880
  • [19] Electrochemical diselenylation of indolizines via intermolecular C-Se formation with 2-methylpyridines, α-bromoketones and diselenides
    Li, Junxuan
    Liu, Xiang
    Deng, Jiadi
    Huang, Yingshan
    Pan, Zihao
    Yu, Yue
    Cao, Hua
    [J]. CHEMICAL COMMUNICATIONS, 2020, 56 (05) : 735 - 738
  • [20] Synthesis of Naphtho[1′,2′:4,5]imidazo[1,2-α]pyridines and imidazo[5,1,2-cd]indolizines Through Pd-Catalyzed Cycloaromatization of 2-Phenylimidazo[1,2-α]pyridines with Alkynes
    Li, Peiyuan
    Zhang, Xinying
    Fan, Xuesen
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (15) : 7508 - 7518