Synthesis of Indolizines from Pyridinium Salts and Ethyl Bromodifluoroacetate

被引:46
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, V1, P157
[2]   A New Simple Procedure for the Synthesis of Heptamethyl Cyclohepta-1,3,5-triene-1,2,3,4,5,6,7-heptacarboxylate [J].
Belyy, Alexander Yu. ;
Platonov, Dmitry N. ;
Salikov, Rinat F. ;
Levina, Anastasiya A. ;
Tomilov, Yury V. .
SYNLETT, 2018, 29 (09) :1157-1160
[3]   Synthesis of 2-Aminoindolizines by 1,3-Dipolar Cycloaddition of Pyridinium Ylides with Electron-Deficient Ynamides [J].
Brioche, Julien ;
Meyer, Christophe ;
Cossy, Janine .
ORGANIC LETTERS, 2015, 17 (11) :2800-2803
[4]   Slicing and Splicing of Bromodifluoro-N-arylacetamides: Dearomatization and Difunctionalization of Pyridines [J].
Chen, Hongtai ;
Yang, Yanyan ;
Wang, Lianxin ;
Niu, Yuxiang ;
Guo, Minjie ;
Ren, Xiangwei ;
Zhao, Wentao ;
Tang, Xiangyang ;
Wang, Guangwei .
ORGANIC LETTERS, 2020, 22 (16) :6610-6616
[5]   Discovery and Characterization of GSK2801, a Selective Chemical Probe for the Bromodomains BAZ2A and BAZ2B [J].
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. .
JOURNAL OF MEDICINAL CHEMISTRY, 2016, 59 (04) :1410-1424
[6]   Two-Component Approach Toward a Fully Substituted N-Fused Pyrrole Ring [J].
Chernyak, Dmitri ;
Skontos, Cathy ;
Gevorgyan, Vladimir .
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 [J].
Choi, Eun Joung ;
Kim, Eunha ;
Lee, Youngjun ;
Jo, Ala ;
Park, Seung Bum .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (05) :1346-1350
[8]   Synthesis, anticonvulsant, and anti-inflammatory activities of some new benzofuran-based heterocycles [J].
Dawood, KM ;
Abdel-Gawad, H ;
Ellithey, M ;
Mohamed, HA ;
Hegazi, B .
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 [J].
Deng, Jian-Chao ;
Gao, Yong-Chao ;
Zhu, Zhu ;
Xu, Li ;
Li, Zhao-Dong ;
Tang, Ri-Yuan .
ORGANIC LETTERS, 2019, 21 (02) :545-548
[10]   SYNTHESIS OF INDOLIZINES STARTING FROM PYRYLIUM-SALTS [J].
DINCULESCU, A ;
BALABAN, TS ;
BALABAN, AT .
TETRAHEDRON LETTERS, 1987, 28 (27) :3145-3146