One-pot sequential reactions for the synthesis of versatile 11C-labeled olefin frameworks

被引:4
作者
Takashima, Misato [1 ]
Kato, Koichi [2 ]
Ogawa, Mikako [1 ]
Magata, Yasuhiro [1 ]
机构
[1] Hamamatsu Univ, Sch Med, Med Photon Res Ctr, Hamamatsu, Shizuoka 4313192, Japan
[2] Natl Ctr Neurol & Psychiat, Dept Integrat Brain Imaging, Kodaira, Tokyo 1878551, Japan
基金
日本学术振兴会;
关键词
BORONIC ACID-ESTERS; RAPID METHYLATION; CARBON FRAMEWORKS; PET TRACERS; EMISSION; IODIDE;
D O I
10.1039/c3ra43636e
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A simple and efficient methodology to construct C-11-labeled olefins (5) was developed. The method involves two different C-C bond-forming reactions: C-11-methylation of a phosphonate (2) using [C-11] methyl iodide (1) and subsequent HWE reaction of C-11-methylated phosphonate (3) with aldehydes (4). Tetrabutylammonium fluoride promoted both C-C bond-forming reactions efficiently as a base. This sequential reaction was conducted in one pot. A wide variety of alpha-[C-11] methyl-alpha,beta-unsaturated compounds were prepared by changing the substituents on the phosphonate and the aldehyde.
引用
收藏
页码:21275 / 21279
页数:5
相关论文
共 28 条
[1]   Molecular imaging with PET [J].
Ametamey, Simon M. ;
Honer, Michael ;
Schubiger, Pius August .
CHEMICAL REVIEWS, 2008, 108 (05) :1501-1516
[2]   Functionalisation of 11C-labelled olefins via a Heck coupling reaction [J].
Björkman, M ;
Långström, B .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (18) :3031-3034
[3]   P[N(i-Bu)CH2CH2]3N: Nonionic Lewis Base for Promoting the Room-Temperature Synthesis of α,β-Unsaturated Esters, Fluorides, Ketones, and Nitriles Using Wadsworth-Emmons Phosphonates [J].
Chintareddy, Venkat Reddy ;
Ellern, Arkady ;
Verkade, John G. .
JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (21) :7166-7174
[4]   Multimodality molecular imaging with combined optical and SPECT/PET modalities [J].
Culver, Joseph ;
Akers, Walter ;
Achilefu, Samuel .
JOURNAL OF NUCLEAR MEDICINE, 2008, 49 (02) :169-172
[5]   Palladium(0)-Mediated Rapid Methylation and Fluoromethylation on Carbon Frameworks by Reacting Methyl and Fluoromethyl Iodide with Aryl and Alkenyl Boronic Acid Esters: Useful for the Synthesis of [11C]CH3-C- and [18F]FCH2-C-Containing PET Tracers (PET=Positron Emission Tomography) [J].
Doi, Hisashi ;
Ban, Ikuya ;
Nonoyama, Akihito ;
Sumi, Kengo ;
Kuang, Chunxiang ;
Hosoya, Takamitsu ;
Tsukada, Hideo ;
Suzuki, Masaaki .
CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (16) :4165-4171
[6]   Microwave-enhanced radiochemistry [J].
Elander, N ;
Jones, JR ;
Lu, SY ;
Stone-Elander, S .
CHEMICAL SOCIETY REVIEWS, 2000, 29 (04) :239-249
[7]   Synthesis of [11C]/[13C]acrylamides by palladium-mediated carbonylation [J].
Eriksson, Jonas ;
Aberg, Ola ;
Langstrom, Bengt .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (03) :455-461
[8]   PHOSPHORORGANISCHE VERBINDUNGEN .20. PHOSPHINOXYDE ALS OLEFINIERUNGSREAGENZIEN [J].
HORNER, L ;
HOFFMANN, H ;
WIPPEL, HG ;
KLAHRE, G .
CHEMISCHE BERICHTE-RECUEIL, 1959, 92 (10) :2499-2505
[9]   Rapid methylation on carbon frame works for pet tracer synthesis: Part 7.: Rapid methylation on carbon frameworks useful for the synthesis of 11C H3-incorporated PET tracers:: Pd(0)-mediated rapid coupling of methyl iodide with an alkenyltributylstannane leading to a 1-methylalkenetl [J].
Hosoya, T ;
Sumi, K ;
Doi, H ;
Wakao, M ;
Suzuki, M .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (03) :410-415
[10]  
Johnson A. W., 1993, YLIDES IMINES PHOSPH, P307