Regioselective Synthesis of Thiocyanate-Containing Isoxazolines via FeIII/K2S2O8-Mediated Radical Thiocyanation/Cyclization Cascade Reaction of β, γ-Unsaturated Oximes

被引:22
作者
Ji, Fei [1 ]
Fan, Yun [1 ]
Yang, Run [1 ]
Yang, Yueyan [1 ]
Yu, Dianwen [1 ]
Wang, Minyu [1 ]
Li, Zhiyu [2 ]
机构
[1] China Pharmaceut Univ, Dept Pharmaceut Engn, 639 Longmian Ave, Nanjing 211198, Jiangsu, Peoples R China
[2] China Pharmaceut Univ, Dept Med Chem, 24 Tongjiaxiang, Nanjing 210009, Jiangsu, Peoples R China
关键词
cyclization; isoxazolines; radical reactions; thiocyanation; beta; gamma-unsaturated oximes; NITRILE OXIDE CYCLOADDITIONS; BETA; GAMMA-UNSATURATED OXIMES; UNACTIVATED ALKENES; C-3; THIOCYANATION; FACILE SYNTHESIS; AMINO ACIDS; DELTA(2)-ISOXAZOLINES; CYCLIZATION; ROUTE; SUBSTITUENT;
D O I
10.1002/ajoc.201700050
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A simple approach for the synthesis of thiocyanate-containing isoxazolines by FeIII/K2S2O8 mediated radical thiocyanation/cyclization cascade reaction of accessible beta,gamma-unsaturated oximes has been developed. The high selectivity, mild reaction conditions and absence of harmful heavy-metal reagents render this reaction attractive. Additionally, the thiocyanate group from isoxazolines could be easily converted to various important functional groups, which could make these compounds important building blocks in organic synthesis.
引用
收藏
页码:682 / 685
页数:4
相关论文
共 53 条
[1]   A new asymmetric Wacker-type cyclization and tandem cyclization promoted by Pd(II)-spiro bis(isoxazoline) catalyst [J].
Arai, MA ;
Kuraishi, M ;
Arai, T ;
Sasai, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (12) :2907-2908
[2]   Design and synthesis of the first spiro bis(isoxazoline) derivatives as asymmetric ligands [J].
Arai, MA ;
Arai, T ;
Sasai, H .
ORGANIC LETTERS, 1999, 1 (11) :1795-1797
[3]  
Bode JW, 2001, ANGEW CHEM INT EDIT, V40, P2082, DOI 10.1002/1521-3773(20010601)40:11<2082::AID-ANIE2082>3.0.CO
[4]  
2-1
[5]   A mild and chemoselective method for the reduction of conjugated isoxazolines to β-hydroxy ketones [J].
Bode, JW ;
Carreira, EM .
ORGANIC LETTERS, 2001, 3 (10) :1587-1590
[6]   Stereoselective syntheses of epothilones A and B via nitrile oxide cycloadditions and related studies [J].
Bode, JW ;
Carreira, EM .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (19) :6410-6424
[7]  
BODE JW, 2001, ANGEW CHEM, V113, P2128
[8]   Amphipathic Small Molecules Mimic the Binding Mode and Function of Endogenous Transcription Factors [J].
Buhrlage, Sara J. ;
Bates, Caleb A. ;
Rowe, Steven P. ;
Minter, Aaron R. ;
Brennan, Brian B. ;
Majmudar, Chinmay Y. ;
Wemmer, David E. ;
Al-Hashimi, Hashim ;
Mapp, Anna K. .
ACS CHEMICAL BIOLOGY, 2009, 4 (05) :335-344
[9]   SYNTHESIS OF 2,2,2-TRIFLUOROETHANESULFONIC ACID [J].
BUNYAGIDJ, C ;
PIOTROWSKA, H ;
ALDRIDGE, MH .
JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (16) :3335-3336
[10]   Synthesis and Biochemical Evaluation of Δ2-Isoxazoline Derivatives as DNA Methyltransferase 1 Inhibitors [J].
Castellano, Sabrina ;
Kuck, Dirk ;
Viviano, Monica ;
Yoo, Jakyung ;
Lopez-Vallejo, Fabian ;
Conti, Paola ;
Tamborini, Lucia ;
Pinto, Andrea ;
Medina-Franco, Jose L. ;
Sbardella, Gianluca .
JOURNAL OF MEDICINAL CHEMISTRY, 2011, 54 (21) :7663-7677