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Synthesis 2008(15): 2439-2445
DOI: 10.1055/s-2008-1067158
DOI: 10.1055/s-2008-1067158
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Synthesis of Benzimidazoles Condensed with, or Linked to, Nitroxides or Heterocyclic N-Oxides
Weitere Informationen
Received
3 April 2008
Publikationsdatum:
08. Juli 2008 (online)
Publikationsverlauf
Publikationsdatum:
08. Juli 2008 (online)
Abstract
Pyrazino[1,2-a]benzimidazoles were synthesized starting from 2-acetyl-1H-benzimidazole. Benzimidazoles were linked to nitroxides by lithiation and ring-closure and cross-coupling reactions leading to pH-sensitive EPR probes and a paramagnetic analogue of antiviral agent HBB.
Key words
cross-coupling - free radicals - heterocycles - lithiation - ring closure
-
1a
Wright JB. Chem. Rev. 1951, 48: 397 -
1b
Preston PN. Chem. Rev. 1974, 74: 279 -
1c
Benzimidazoles
and Congeneric Tricyclic Compounds
Preston PN. Wiley; New York: 1980. -
1d
Grimmett MS. Imidazole and Benzimidazole Synthesis Academic Press; London: 1997. - 2
Chassaing C.Berger M.Heckeroth A.Ilg T.Jaeger M.Kern C.Schmid K.Uphoff M. J. Med. Chem. 2008, 51: 1111 - 3
O’Shaughnessy J.Aldabbagh F. Synthesis 2005, 1069 - 4
Kromer W. Digestion 1995, 56: 443 - 5
White AW.Almassy R.Calvert AH.Curtin NJ.Griffin RJ.Hostomsky Z.Maegley K.Newell DR.Srinivasan S.Golding BT. J. Med. Chem. 2000, 43: 4084 - 6
Hankovszky HO.Hideg K.Lex L.Földesi A.Sohár P. J. Chem. Soc., Perkin Trans. 1 1980, 699 - 7
Hideg K.Kálai T.Sár CP. J. Heterocycl. Chem. 2005, 42: 437 - 8
Hankovszky HO.Hideg K.Lovas J.Jerkovich G.Rockenbauer A.Gyõr M.Sohár P. Can. J. Chem. 1989, 67: 1392 - 9
Kálai T.Jekõ J.Hideg K. Synthesis 2000, 831 - 10
Kulcsár G.Kálai T.Jekõ J.Hideg K. Synthesis 2003, 1361 - 11
Mózsik G.Peidl Z.Szolcsányi J.Dömötör A.Hideg K.Szekeres G.Karádi O.Hunyady B. Inflammopharmacology 2005, 13: 139 - 12
Matrick H.Day AR. J. Org. Chem. 1961, 26: 1511 - 13
Edwards WB.Day AR. J. Org. Chem. 1974, 39: 1519 - 14
Hideg K.Hankovszky HO. Synthesis 1978, 313 - 15
Demoirayak S.Mohsen AU.Karaburun AC. Eur. J. Med. Chem. 2002, 37: 255 - 16
Abbiati G.Arcadi A.Billinazzi A.Beccalli E.Rossi E.Zanzola S. J. Org. Chem. 2005, 70: 4088 - 17
Serafin B.Glowczyk J. Rocz. Chem. 1976, 50: 1211 ; Chem. Abstr. 1977, 86, 43618 - 18
Hideg K.Hankovszky HO.Lex L.Kulcsár G. Synthesis 1980, 911 - 19
Nadipuram AK.David WM.Kumar D.Kerwin SM. Org. Lett. 2002, 4: 4543 - 20
Katritzky AR.Akutagawa K. J. Org. Chem. 1989, 54: 2949 - 21
Hideg K.Hankovszky HO. Acta Chim. Acad. Sci. Hung. 1966, 49: 303 ; Chem. Abstr. 1968, 69, 51956 - 22
Bottle SE.Gillies DG.Hughes DL.Micallef AS.Smirnov AI.Sutcliffe LH. J. Chem. Soc., Perkin Trans. 2 2000, 1285 - 23
Eggers HJ.Tamm I. Nature 1963, 197: 1327 - 24
Potapenko DI.Foster MA.Lurie DJ.Kirilyuk IA.Hutchison JMS.Grigor’ev IA.Bagryanskaya EG.Khramtsov VV. J. Magn. Reson. 2006, 182: 1 - 25
Dornow A.Muller A. Chem. Ber. 1960, 93: 41 - 26
Dubey PK.Kumar CR.Babu B. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 2003, 42: 3128 - 27
Kálai T.Balog M.Jekõ J.Hideg K. Synthesis 1999, 973 - 28
Delpierre GR.Lamchen M. J. Chem. Soc. 1963, 4693 - 29
Tasz MK.Plenat F.Cristau HJ.Skowronski R. Phosphorus, Sulfur Silicon Relat. Elem. 1991, 57: 143 - 30
Popov II.Tkachenko PV.Simonov AM. Khim. Geterotsikl. Soedin. 1973, 551 ; Chem. Abstr. 1973, 79, 31984