Radiochemical F-18-fluoroarylation of unsaturated alpha-, beta- and gamma-amino acids, application to a radiolabelled analogue of baclofen
Unsaturated alpha-, beta- and gamma-amino acids have been investigated as substrates for the reductive Meerwein arylation. Radical reactions of this type have been shown to be a valuable tool for the fast and efficient introduction of the 4-[F-18]fluorophenyl group into precursor molecules allowing...
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| Published in | Tetrahedron Vol. 64; no. 52; pp. 11846 - 11851 |
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| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
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22.12.2008
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| Abstract | Unsaturated alpha-, beta- and gamma-amino acids have been investigated as substrates for the reductive Meerwein arylation. Radical reactions of this type have been shown to be a valuable tool for the fast and efficient introduction of the 4-[F-18]fluorophenyl group into precursor molecules allowing short-time syntheses of potential PET radiotracers, which would be more difficult to access by other methods. (C) 2008 Elsevier Ltd. All rights reserved. |
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| AbstractList | Unsaturated alpha-, beta- and gamma-amino acids have been investigated as substrates for the reductive Meerwein arylation. Radical reactions of this type have been shown to be a valuable tool for the fast and efficient introduction of the 4-[F-18]fluorophenyl group into precursor molecules allowing short-time syntheses of potential PET radiotracers, which would be more difficult to access by other methods. (C) 2008 Elsevier Ltd. All rights reserved. |
| Author | Heinrich, Markus R. Hoefling, Sarah B. Wester, Hans-Juergen Hultsch, Christina |
| Author_xml | – sequence: 1 givenname: Sarah B. surname: Hoefling fullname: Hoefling, Sarah B. organization: Tech Univ Munich, D-85747 Garching, Germany – sequence: 2 givenname: Christina surname: Hultsch fullname: Hultsch, Christina organization: Tech Univ Munich, Klinikum Rechts Isar, Nukl Med Klin & Poliklin, D-81675 Munich, Germany – sequence: 3 givenname: Hans-Juergen surname: Wester fullname: Wester, Hans-Juergen organization: Tech Univ Munich, Klinikum Rechts Isar, Nukl Med Klin & Poliklin, D-81675 Munich, Germany – sequence: 4 givenname: Markus R. orcidid: 0000-0001-7113-2025 surname: Heinrich fullname: Heinrich, Markus R. email: markus.heinrich@ch.tum.de organization: Tech Univ Munich, D-85747 Garching, Germany |
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| Keywords | POLAR ARENEDIAZONIUM RESOLUTION CHEMISTRY GABA ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS SALTS BINDING (R)-BACLOFEN PEPTIDE |
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| References | Phelps, ME (WOS:000086393400027) 2000; 41 Costantino, G (WOS:000168841500018) 2001; 44 GRIGG, R (WOS:A1992JX10900010) 1992; 48 Kung, HF (WOS:000172745300059) 2001; 123 ALLAN, RD (WOS:A1990CY09900027) 1990; 46 RAMBAUD M (WOS:000262031500005.28) 1993; 8 ALLAN, RD (WOS:A1978FW63800021) 1978; 31 RAMBAUD M (WOS:000262031500005.27) 1988; 66 STELLA L (WOS:000262031500005.30) 2001; 1 TYAGI, OD (WOS:A1992KA36400013) 1992; 31 BERTHELOT, P (WOS:A1991GB15800033) 1991; 34 CITTERIO, A (WOS:A1982MX12200017) 1982; 47 HERDEIS, C (WOS:A1992JN76800019) 1992; 3 OBUSHAK ND (WOS:000262031500005.23) 1983; 19 BIRKHOFER H (WOS:000262031500005.5) 1987; 99 Langlois, N (WOS:A1996VU39800005) 1996; 52 DURRMANN H (WOS:000262031500005.12) 1979; 112 LIU, S (WOS:A1992HK86000012) 1992; 35 Olma, S (WOS:000242335900002) 2006; 49 YOSHIFUJI, S (WOS:A1995RR08500007) 1995; 43 BYUN, HS (WOS:A1994MY72600017) 1994; 35 VILLIERAS, J (WOS:A1982PP33000008) 1982 CITTERIO, A (WOS:A1980JQ10300006) 1980 BIRKHOFER, H (WOS:A1987J197200022) 1987; 26 Hultsch, C (WOS:000253785600037) 2008; 49 Patt, JT (WOS:000180182900004) 2002; 45 FELIU, AL (WOS:A1988Q746100010) 1988; 25 GALLI, C (WOS:A1988P702300004) 1988; 88 Ross, TL (WOS:000247563100064) 2007; 129 Tulla-Puchet, J (WOS:000227197400025) 2005; 61 MERKUSHEV, EB (WOS:A1988R288100001) 1988 Le Bars, D (WOS:000242744300007) 2006; 127 CITTERIO, A (WOS:A1986C074600010) 1986 SINGH, R (WOS:A1990CM13700046) 1990; 112 Cai, LS (WOS:000257045000001) 2008; 2008 |
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AN EASY SYNTHESIS OF ETHYL ALPHA-HYDROXYMETHYLACRYLATE AND ETHYL ALPHA-HALOMETHYLACRYLATES USING FORMALDEHYDE IN WATER publication-title: SYNTHESIS-STUTTGART contributor: fullname: VILLIERAS, J – volume: 8 start-page: 265 year: 1993 ident: WOS:000262031500005.28 publication-title: ORG SYNTH contributor: fullname: RAMBAUD M – start-page: 291 year: 1980 ident: WOS:A1980JQ10300006 article-title: 2-ARYLALKYL KETONES AND 3-ARYLALKANALS FROM ARENEDIAZONIUM SALTS AND ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS publication-title: SYNTHESIS-STUTTGART contributor: fullname: CITTERIO, A – volume: 129 start-page: 8018 year: 2007 ident: WOS:000247563100064 article-title: Nucleophilic F-18-Fluorination of heteroaromatic iodonium salts with no-carrier-added [F-18]Fluoride publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja066850h contributor: fullname: Ross, TL – volume: 35 start-page: 1371 year: 1994 ident: WOS:A1994MY72600017 article-title: IMPROVED SYNTHESES OF ETHYL ALPHA-(BROMOMETHYL)ACRYLATE AND 2-METHYLENE-1,3-PROPANEDIOL VIA ETHYL ALPHA-(HYDROXYMETHYL)ACRYLATE publication-title: TETRAHEDRON LETTERS contributor: fullname: BYUN, HS – volume: 3 start-page: 1213 year: 1992 ident: WOS:A1992JN76800019 article-title: SYNTHESIS OF HOMOCHIRAL R-BACLOFEN FROM S-GLUTAMIC ACID publication-title: TETRAHEDRON-ASYMMETRY contributor: fullname: HERDEIS, C – volume: 88 start-page: 765 year: 1988 ident: WOS:A1988P702300004 article-title: RADICAL REACTIONS OF ARENEDIAZONIUM IONS - AN EASY ENTRY INTO THE CHEMISTRY OF THE ARYL RADICAL publication-title: CHEMICAL REVIEWS contributor: fullname: GALLI, C – start-page: 308 year: 1986 ident: WOS:A1986C074600010 article-title: REDUCTIVE ARYLATION OF MALEIC AND FUMARIC-ACID DERIVATIVES BY ARENEDIAZONIUM AND TITANIUM(III) SALTS publication-title: SYNTHESIS-STUTTGART contributor: fullname: CITTERIO, A – volume: 31 start-page: 2283 year: 1978 ident: WOS:A1978FW63800021 article-title: SYNTHESIS OF SOME SUBSTITUTED 4-AMINOBUT-2-ENOIC ACIDS AS ANALOGS OF NEUROTRANSMITTER GABA publication-title: AUSTRALIAN JOURNAL OF CHEMISTRY contributor: fullname: ALLAN, RD – volume: 47 start-page: 81 year: 1982 ident: WOS:A1982MX12200017 article-title: STERIC, POLAR, AND RESONANCE EFFECTS IN REACTIVITY AND REGIOSELECTIVITY OF ARYL RADICAL-ADDITION TO ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: CITTERIO, A – volume: 127 start-page: 1488 year: 2006 ident: WOS:000242744300007 article-title: Fluorine-18 and medical imaging: Radiopharmaceuticals for positron emission tomography publication-title: JOURNAL OF FLUORINE CHEMISTRY doi: 10.1016/j.jfluchem.2006.09.015 contributor: fullname: Le Bars, D – volume: 19 start-page: 1391 year: 1983 ident: WOS:000262031500005.23 publication-title: J ORG CHEM USSR contributor: fullname: OBUSHAK ND |
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| Title | Radiochemical F-18-fluoroarylation of unsaturated alpha-, beta- and gamma-amino acids, application to a radiolabelled analogue of baclofen |
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