Synthesis of Indolizines from Pyridinium Salts and Ethyl Bromodifluoroacetate

被引:42
作者
Hou, Xiaoya [1 ]
Zhou, Sen [1 ]
Li, Yuli [1 ]
Guo, Minjie [2 ]
Zhao, Wentao [1 ]
Tang, Xiangyang [1 ]
Wang, Guangwei [1 ]
机构
[1] Tianjin Univ, Sch Sci, Dept Chem, Tianjin Key Lab Mol Optoelect Sci, Tianjin 300072, Peoples R China
[2] Tianjin Univ, Sch Pharmaceut Sci & Technol, Inst Mol Design & Synth, Tianjin 300072, Peoples R China
关键词
1,3-DIPOLAR CYCLOADDITION; FUNCTIONALIZED INDOLIZINES; DIRECT DIFLUOROMETHYLATION; DERIVATIVES; YLIDES; DIFLUOROALKYLATION; PHARMACEUTICALS; FLUORINE; ALCOHOLS; ALKENES;
D O I
10.1021/acs.orglett.0c03540
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Here we present a novel annulation of pyridinium salts with BrCF2CO2 Et to access the indolizine derivatives with high efficiency. The alpha substitution of pyridine plays a key role in determining the reaction pathways. Various types of indolizines can be conveniently accessed from easily available pyridinium salts under mild and simple reaction conditions.
引用
收藏
页码:9313 / 9318
页数:6
相关论文
共 69 条
  • [1] Babaev E.V., 2014, FLUORINE HETEROCYCLI, P157
  • [2] A New Simple Procedure for the Synthesis of Heptamethyl Cyclohepta-1,3,5-triene-1,2,3,4,5,6,7-heptacarboxylate
    Belyy, Alexander Yu.
    Platonov, Dmitry N.
    Salikov, Rinat F.
    Levina, Anastasiya A.
    Tomilov, Yury V.
    [J]. SYNLETT, 2018, 29 (09) : 1157 - 1160
  • [3] Synthesis of 2-Aminoindolizines by 1,3-Dipolar Cycloaddition of Pyridinium Ylides with Electron-Deficient Ynamides
    Brioche, Julien
    Meyer, Christophe
    Cossy, Janine
    [J]. ORGANIC LETTERS, 2015, 17 (11) : 2800 - 2803
  • [4] Slicing and Splicing of Bromodifluoro-N-arylacetamides: Dearomatization and Difunctionalization of Pyridines
    Chen, Hongtai
    Yang, Yanyan
    Wang, Lianxin
    Niu, Yuxiang
    Guo, Minjie
    Ren, Xiangwei
    Zhao, Wentao
    Tang, Xiangyang
    Wang, Guangwei
    [J]. ORGANIC LETTERS, 2020, 22 (16) : 6610 - 6616
  • [5] Discovery and Characterization of GSK2801, a Selective Chemical Probe for the Bromodomains BAZ2A and BAZ2B
    Chen, Peiling
    Chaikuad, Apirat
    Bamborough, Paul
    Bantscheff, Marcus
    Bountra, Chas
    Chung, Chun-wa
    Fedorov, Oleg
    Grandi, Paola
    Jung, David
    Lesniak, Robert
    Lindon, Matthew
    Mueller, Susanne
    Philpott, Martin
    Prinjha, Rab
    Rogers, Catherine
    Selenski, Carolyn
    Tallant, Cynthia
    Werner, Thilo
    Willson, Timothy M.
    Knapp, Stefan
    Drewry, David H.
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2016, 59 (04) : 1410 - 1424
  • [6] Two-Component Approach Toward a Fully Substituted N-Fused Pyrrole Ring
    Chernyak, Dmitri
    Skontos, Cathy
    Gevorgyan, Vladimir
    [J]. ORGANIC LETTERS, 2010, 12 (14) : 3242 - 3245
  • [7] Rational Perturbation of the Fluorescence Quantum Yield in Emission-Tunable and Predictable Fluorophores (Seoul-Fluors) by a Facile Synthetic Method Involving C-H Activation
    Choi, Eun Joung
    Kim, Eunha
    Lee, Youngjun
    Jo, Ala
    Park, Seung Bum
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (05) : 1346 - 1350
  • [8] Synthesis, anticonvulsant, and anti-inflammatory activities of some new benzofuran-based heterocycles
    Dawood, KM
    Abdel-Gawad, H
    Ellithey, M
    Mohamed, HA
    Hegazi, B
    [J]. ARCHIV DER PHARMAZIE, 2006, 339 (03) : 133 - 140
  • [9] Sulfite-Promoted Synthesis of N-Difluoromethylthioureas via the Reaction of Azoles with Bromodifluoroacetate and Elemental Sulfur
    Deng, Jian-Chao
    Gao, Yong-Chao
    Zhu, Zhu
    Xu, Li
    Li, Zhao-Dong
    Tang, Ri-Yuan
    [J]. ORGANIC LETTERS, 2019, 21 (02) : 545 - 548
  • [10] SYNTHESIS OF INDOLIZINES STARTING FROM PYRYLIUM-SALTS
    DINCULESCU, A
    BALABAN, TS
    BALABAN, AT
    [J]. TETRAHEDRON LETTERS, 1987, 28 (27) : 3145 - 3146