ELECTROLYTIC PARTIAL FLUORINATION OF ORGANIC-COMPOUNDS .19. A NOVEL SYNTHESIS OF FLUOROTHIENO[2,3-B]PYRIDINES USING ANODIC FLUORINATION OF HETEROCYCLIC SULFIDES AS A KEY STEP

被引:44
作者
ERIAN, AW [1 ]
KONNO, A [1 ]
FUCHIGAMI, T [1 ]
机构
[1] TOKYO INST TECHNOL,DEPT ELECTR CHEM,MIDORI KU,YOKOHAMA,KANAGAWA 226,JAPAN
关键词
D O I
10.1021/jo00128a044
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Highly regioselective anodic monofluorination of 2-pyridyl and C-pyrimidinyl sulfides bearing various electron-withdrawing groups were successfully carried out. The fluorinated sulfides were easily converted into 2-fluorothieno[2,3-b]pyridines in good yields.
引用
收藏
页码:7654 / 7659
页数:6
相关论文
共 32 条
[1]   ELECTROCHEMICAL MONOFLUORINATION OF PYRIDINE - SYNTHESIS OF 2-FLUOROPYRIDINE AT A PLATINUM ANODE [J].
BALLINGER, JR ;
TEARE, FW ;
BOWEN, BM ;
GARNETT, ES .
ELECTROCHIMICA ACTA, 1985, 30 (08) :1075-1077
[2]   STUDIES ON ALKYLHETEROAROMATIC COMPOUNDS - THE REACTIVITY OF ALKYL POLYFUNCTIONALLY SUBSTITUTED AZINES TOWARDS ELECTROPHILIC REAGENTS [J].
ELNAGDI, MH ;
ABDELRAZEK, FM ;
IBRAHIM, NS ;
ERIAN, AW .
TETRAHEDRON, 1989, 45 (11) :3597-3604
[3]  
Filler R., 1982, BIOMEDICAL ASPECTS F
[4]   ELECTROLYTIC REACTIONS OF FLUOROORGANIC COMPOUNDS .14. REGIOSELECTIVE ANODIC METHOXYLATION OF N-(FLUOROETHYL)AMINES - PREPARATION OF HIGHLY USEFUL FLUOROALKYLATED BUILDING-BLOCKS [J].
FUCHIGAMI, T ;
ICHIKAWA, S .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (03) :607-615
[5]   ELECTROLYTIC REACTIONS OF FLUORO ORGANIC-COMPOUNDS .7. ANODIC METHOXYLATION AND ACETOXYLATION OF 2,2,2-TRIFLUOROETHYL SULFIDES - PREPARATION OF HIGHLY USEFUL TRIFLUOROMETHYLATED BUILDING-BLOCKS [J].
FUCHIGAMI, T ;
YAMAMOTO, K ;
NAKAGAWA, Y .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (01) :137-142
[6]   ELECTROLYTIC PARTIAL FLUORINATION OF ORGANIC-COMPOUNDS .17. REGIOSPECIFIC ANODIC FLUORINATION OF SULFIDES BEARING ELECTRON-WITHDRAWING SUBSTITUENTS AT THE POSITION-ALPHA TO THE SULFUR ATOM [J].
FUCHIGAMI, T ;
SHIMOJO, M ;
KONNO, A .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (11) :3459-3464
[7]   ELECTROLYTIC PARTIAL FLUORINATION OF ORGANIC-COMPOUNDS .1. REGIOSELECTIVE ANODIC MONOFLUORINATION OF ORGANOSULFUR COMPOUNDS [J].
FUCHIGAMI, T ;
SHIMOJO, M ;
KONNO, A ;
NAKAGAWA, K .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (25) :6074-6075
[8]   ELECTROLYTIC PARTIAL FLUORINATION OF ORGANIC-COMPOUNDS .12. SELECTIVE ANODIC MONOFLUORINATION OF FLUOROALKYL AND ALKYL SULFIDES [J].
FUCHIGAMI, T ;
KONNO, A ;
NAKAGAWA, K ;
SHIMOJO, M .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (20) :5937-5941
[9]  
FUCHIGAMI T, 1994, REV HETEROATOM CHEM, V10, P155
[10]  
FUCHIGAMI T, 1993, CURRENT TOPICS ELECT, V2, P155