Preparation of (fluoromethyl)- and (difluoromethyl) imidazoles

被引:8
作者
Dolensky, B [1 ]
Kirk, KL [1 ]
机构
[1] NIDDKD, Bioorgan Chem Lab, NIH, Bethesda, MD 20892 USA
关键词
fluorinated imidazoles; deoxyfluorination; fluorinated heterocycles; Deoxo-Fluor; fluorinations; aldehydes; alcohols;
D O I
10.1135/cccc20021335
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
2-(Fluoromethyl)- and 2-(difluoromethyl)imidazoles, and 4-(fluoromethyl)- and 4-( difluoromethyl) imidazoles have been prepared by deoxyfluorination of (hydroxymethyl) imidazole or formylimidazole precursors.
引用
收藏
页码:1335 / 1344
页数:10
相关论文
共 31 条
[1]   MULTIPLEX PROTON-TRANSFER AND ELECTRON-TRANSFER NATURES BASED ON THE 2,2'-BI-1H-IMIDAZOLE SYSTEM .1. ACID DISSOCIATION-CONSTANTS AND REDOX PROPERTIES IN SOLUTION [J].
AKUTAGAWA, T ;
SAITO, G .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1995, 68 (07) :1753-1773
[2]   BETA-1-SELECTIVE ADRENOCEPTOR ANTAGONISTS - EXAMPLES OF THE 2-[4-[3-(SUBSTITUTED AMINO)-2-HYDROXYPROPOXY]PHENYL]IMIDAZOLE CLASS .2. [J].
BALDWIN, JJ ;
CHRISTY, ME ;
DENNY, GH ;
HABECKER, CN ;
FREEDMAN, MB ;
LYLE, PA ;
PONTICELLO, GS ;
VARGA, SL ;
GROSS, DM ;
SWEET, CS .
JOURNAL OF MEDICINAL CHEMISTRY, 1986, 29 (06) :1065-1080
[3]   STUDIES OF ENZYME-MEDIATED REACTIONS .13. STEREOCHEMICAL COURSE OF THE FORMATION OF HISTAMINE BY DECARBOXYLATION OF (2S)-HISTIDINE WITH ENZYMES FROM CLOSTRIDIUM-WELCHII AND LACTOBACILLUS 30A [J].
BATTERSBY, AR ;
NICOLETTI, M ;
STAUNTON, J ;
VLEGGAAR, R .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1980, (01) :43-51
[4]   Generation of heteroarylium-N-difluoromethylides and heteroaryl-N-difluoromethyl anions and their reactions with electrophiles:: heteroaryl- and heteroarylium-N-difluoromethyl trimethylsilanes and a new heteroaryl-N-trifluoromethane [J].
Bissky, G ;
Röschenthaler, GV ;
Lork, E ;
Barten, J ;
Médebielle, M ;
Staninets, V ;
Kolomeitsev, AA .
JOURNAL OF FLUORINE CHEMISTRY, 2001, 109 (02) :173-181
[5]  
Bissky G, 2001, SYNLETT, P374
[6]   New building blocks for fluorinated imidazole derivatives:: Preparation of β-fluoro- and β,β-difluorohistamine [J].
Dolensky, B ;
Kirk, KL .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (13) :4687-4691
[7]   Synthesis of 4,5-difluoroimidazole [J].
Dolensky, B ;
Takeuchi, Y ;
Cohen, LA ;
Kirk, KL .
JOURNAL OF FLUORINE CHEMISTRY, 2001, 107 (01) :147-148
[8]   PREPARATION OF ALPHA-TRIFLUOROMETHYL ESTERS FROM MALONIC ESTERS [J].
EVERETT, TS ;
PURRINGTON, ST ;
BUMGARDNER, CL .
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (20) :3702-3706
[9]  
FAN J, 2002, IN PRESS J FLUORINE
[10]   Syntheses of (trifluoromethyl)imidazoles with additional electronegative substituents. An approach to receptor-activated affinity labels [J].
Hayakawa, Y ;
Kimoto, H ;
Cohen, LA ;
Kirk, KL .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (25) :9448-9454