Abstract
Starting from readily available paramagnetic five- and six-membered ketones and pyrroline
aldehyde, a range of spin labeled heterocycles such as benzazoles, pyrrole, oxazole,
quinoline, benzofuran, thiadiazole have been synthesized in both ‘classical’ and Pd-catalyzed
reactions. These methods were used in the synthesis of paramagnetic ligands such as
oxin and porphyrin.
Key words
free radicals - heterocycles - ketones - ligands - palladium
References
<A NAME="RP03406SS-1">1 </A>
Pozharskii AF.
Soldatenkov AT.
Katritzky AR.
Heterocycles in Life and Society
Wiley;
Chichester:
1997.
<A NAME="RP03406SS-2">2 </A>
Columbus L.
Kálai T.
Jekő J.
Hideg K.
Hubbell WL.
Biochemistry
2001,
40:
3828
<A NAME="RP03406SS-3">3 </A>
Bobbit JM.
Merbouh N.
Org. Synth.
2005,
82:
80
<A NAME="RP03406SS-4">4 </A>
Blough NV.
Simpson DJ.
J. Am. Chem. Soc.
1988,
110:
1915
<A NAME="RP03406SS-5">5 </A>
Hoffman A.
Goldstein S.
Samuni A.
Borman JB.
Schwalb H.
Biochem. Pharmacol.
2003,
66:
1279
<A NAME="RP03406SS-6">6 </A>
Glebska J.
Pulaski L.
Gwozdinski K.
Skolimowski J.
Biometals
2001,
14:
159
<A NAME="RP03406SS-7">7 </A>
Oh S.
Kim K.
Lee BH.
Shim SE.
Choe S.
J. Polym. Sci., Part A: Polym. Chem.
2006,
44:
62
<A NAME="RP03406SS-8">8 </A>
Rozantsev EG.
Free Nitroxide Radicals
Plenum Press;
New York:
1970.
<A NAME="RP03406SS-9">9 </A>
Kálai T.
Balog M.
Jekő J.
Hideg K.
Synthesis
1999,
973
<A NAME="RP03406SS-10">10 </A>
Kálai T.
Balog M.
Jekő J.
Hubbell WL.
Hideg K.
Synthesis
2002,
2365
<A NAME="RP03406SS-11">11 </A>
Kálai T.
Kulcsár G.
Ősz E.
Jekő J.
Sümegi B.
Hideg K.
Arkivoc
2004,
(vii):
266
<A NAME="RP03406SS-12">12 </A>
Kálai T.
Jekő J.
Hideg K.
Synthesis
2000,
831
<A NAME="RP03406SS-13">13 </A>
Kálai T.
Balog M.
Jekő J.
Hideg K.
Synthesis
1998,
1476
<A NAME="RP03406SS-14">14 </A>
Kálai T.
Jekő J.
Hideg K.
Tetrahedron Lett.
2004,
45:
8395
<A NAME="RP03406SS-15">15 </A>
Kálai T.
Jekő J.
Berente Z.
Hideg K.
Synthesis
2006,
439
<A NAME="RP03406SS-16">16 </A>
Kulcsár G.
Kálai T.
Jekő J.
Hideg K.
Synthesis
2003,
1361
<A NAME="RP03406SS-17">17 </A>
Hideg K.
Hankovszky HO.
Lex L.
Kulcsár G.
Synthesis
1980,
911
<A NAME="RP03406SS-18">18 </A>
Stevens MFG.
Shi DF.
Angeles C.
J. Chem. Soc., Perkin Trans. 1
1996,
83
<A NAME="RP03406SS-19">19 </A>
Varma RS.
Saini KR.
Prakash O.
Tetrahedron Lett.
1997,
38:
2621
<A NAME="RP03406SS-20">20 </A>
Hideg K.
Sár PC.
Hankovszky HO.
Tamás T.
Jerkovich G.
Synthesis
1993,
390
<A NAME="RP03406SS-21">21 </A>
Batista RMF.
Costa SPG.
Raposo MMM.
Tetrahedron Lett.
2004,
45:
2825
<A NAME="RP03406SS-22">22 </A>
van Leusen AM.
Hoogenboom BE.
Siderius H.
Tetrahedron Lett.
1972,
13:
2369
<A NAME="RP03406SS-23">23 </A>
Doebner O.
Ber. Dtsch. Chem. Ges.
1887,
20:
277
<A NAME="RP03406SS-24">24 </A>
Hankovszky HO.
Hideg K.
Lex L.
Kulcsár G.
Halász HA.
Can. J. Chem.
1982,
60:
1432
<A NAME="RP03406SS-25">25 </A>
Lindsey JS.
Prathapan S.
Johnson TE.
Wagner RW.
Tetrahedron
1994,
50:
8941
<A NAME="RP03406SS-26">26 </A>
Swamy N.
James DA.
Mohr SC.
Hanson RC.
Ray R.
Bioorg. Med. Chem.
2002,
10:
3237
<A NAME="RP03406SS-27">27 </A>
Ma D.
Cai Q.
Xie X.
Synlett
2005,
1767
<A NAME="RP03406SS-28">28 </A>
Pflum DA. In
Name Reactions in Heterocyclic Chemistry
Li JJ.
Wiley;
Hoboken:
2005.
p.411-415
<A NAME="RP03406SS-29">29 </A>
Hurd CD.
Mori RI.
J. Am. Chem. Soc.
1955,
77:
5359
<A NAME="RP03406SS-30">30 </A>
Suzuki A.
Chem. Commun.
2005,
4759
<A NAME="RP03406SS-31">31 </A>
Alper H.
Van den Hoven BG.
J. Am. Chem. Soc.
2001,
123:
1017
<A NAME="RP03406SS-32">32 </A>
Majo JV.
Prabhakaran J.
Mann JJ.
Kumar JSD.
Tetrahedron Lett.
2003,
44:
8535
<A NAME="RP03406SS-33">33 </A>
Conway SC.
Gribble GW.
Heterocycles
1990,
30:
627
<A NAME="RP03406SS-34">34 </A>
Ram S.
Ehrenkaufer RE.
Synthesis
1988,
91
<A NAME="RP03406SS-35">35 </A>
Chudinov AV.
Rozantsev EG.
Rosinov BV.
Izv. Akad. Nauk. Ser. Khim.
1983,
409 ; Chem. Abstr . 1983 , 98 , 197927
<A NAME="RP03406SS-36">36 </A>
Foy BD.
Smudde RA.
Wood WF.
J. Chem. Educ.
1993,
70:
322
