RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
PDF herunterladen
Synthesis 2003(6): 0871-0878
DOI: 10.1055/s-2003-38694
DOI: 10.1055/s-2003-38694
PAPER
© Georg Thieme Verlag Stuttgart ˙ New YorkGrignard Reagent Addition to 5-Alkylamino-4H-Imidazole 3-Oxides: Synthesis of New pH-Sensitive Spin Probes
Weitere Informationen
Received
6 February 2003
Publikationsdatum:
16. April 2003 (online)
Publikationsverlauf
Publikationsdatum:
16. April 2003 (online)
Abstract
4,4-Dimethyl-4H-imidazole-5-carbaldehyde oxime 3-oxides 4 were prepared by oxidation and nitrosation of 4,5,5-trimethyl-2,5-dihydro-1H-imidazol-1-ols. The oximes 4 were converted to 5-cyano derivatives; the latter react with primary or secondary amines to form 5-(di)alkylamino-4H-imidazole 3-oxides 6. Treatment of 6 with AlkMgX and subsequent oxidation yielded stable nitroxides 4-(di)alkylamino-2,5-dihydroimidazole-1-oxyls 7, the pH-sensitive spin probes.
Key words
Grignard reactions - amines - nitriles - imidazoles - free radicals - spin probes
- 1a
Khramtsov VV.Weiner LM.Grigor’ev IA.Volodarsky LB. Chem. Phys. Lett. 1982, 91: 69 - 1b
Keana JFW.Acarregui MJ.Boyle SLM. J. Am. Chem. Soc. 1982, 104: 926 - 2
Khramtsov VV.Volodarsky LB. In Biological Magnetic Resonance Vol. 14:Berliner LJ. Plenum Press; New York: 1998. p.109MissingFormLabel - 3
Khramtsov VV.Grigor’ev IA.Foster MA.Lurie DJ.Nicholson I. Cell. Mol. Biol. 2000, 46: 1361 - 4
Voinov MA.Martin VV.Volodarskii LB. Bull. Russ. Akad. Sci., Div. Chem. Sci. (Engl.Transl.) 1992, 41: 2091 - 5
Volodarsky LB.Reznikov VA.Grigor’ev IA. In Imidazoline NitroxidesVolodarsky LB. CRC Press; Boca Raton: 1988. p.29MissingFormLabel - 6
Balakirev M.Khramtsov V.Berezina T.Martin V.Volodarsky L. Synthesis 1992, 12: 1223 - 7
Kirilyuk IA.Grigor’ev IA.Volodarsky LB. Izv. Sib. Otd. Akad. Nauk SSSR, Ser. Khim. Nauk 1989, 2: 99 ; Chem. Abstr. 1990, 111, 232670 - 8
Grigor"ev IA.Kirilyuk IA.Volodarskii LB. Chem. Heterocycl. Compd. (Engl.Transl.) 1988, 24: 1355 - 9
Schukin GI.Grigor’ev IA.Volodarsky LB. Izv. Sib. Otd. AN SSSR, Ser. Khim. Nauk. 1984, 4: 81 ; Chem. Abstr. 1985, 102, 11368 - 10
Volodarsky LB.Fust LA.Kobrin VS. Khim Heterocycl. Soedin. 1972, 9: 1246 ; Chem. Abstr. 1973, 78, 4189 - 11
Sammez MP.Katritzky AR. In Advances in Heterocyclic Chemistry Vol. 35:Katritzky AR. Academic Press; New York: 1984. p.413MissingFormLabel - 12
Grigor"ev IA.Shchukin GI.Khramtsov VV.Vainer LM.Starichenko VF.Volodarskii LB. Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl.Transl.) 1985, 34: 2169 - 13
Reznikov VA.Burchak ON.Vishnivetskaya LA.Volodarskii LB.Rybalova TV.Gatilov YuV. Russ. J. Org. Chem. 1997, 33: 1302 - 14
Keana JFW. In Spin Labelling in PharmacologyHoltzman JL. Academic Press; Orlando, Fla.: 1984. p.1MissingFormLabel - 15
Reznikov VA.Volodarsky LB. Tetrahedron 1993, 49: 10669 - 16
Grigor’ev IA.Shchukin GI.Martin VV.Mamatyuk VI. Chem. Heterocycl. Compd. (Engl.Transl.) 1985, 21: 205 - 17
Volodarskii LB.Sevastyanova TK. Zh. Org. Khim. 1971, 8: 1971 ; Chem. Abstr. 1971, 75, 140425 - 18
Khramtsov VV.Weiner LM.Eremenko S.Belchenko OI.Schastnev PV.Grigor’ev IA.Reznikov VA. J. Magn. Res. 1985, 61: 397