Elsevier

Tetrahedron

Volume 51, Issue 39, 25 September 1995, Pages 10771-10794
Tetrahedron

2H-benzimidazoles (isobenzimidazoles). Part 10. Synthesis of polysubstituted o-phenylenediamines and their conversion into heterocycles, particularly 2-substituted benzimidazoles with known or potential anthelminthic activity1.,2.

Dedicated to Professor Dr. Richard Neidlein, Pharmazeutisch-Chemisches Institut, Ruprecht-Karls-Universiat, Heidelberg on the occasion of his 65th birthday (October 25th, 1995).
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Abstract

Polysubstiluted o-phenylenediamines were syathesised in moderate to high yield by reductive cleavage of the corresponding 2H-benzimidazole-2-spirocyclohexane with sodium dithionite in aqueous ethanol and converted into methyl benzimidazole-2-carbamates and 2-methylthio-and 2-trifluoromethylbenzimidazoles with known or potential anthelminthic activity. 5-(Pyrimidin-2-ylthio)-benzimidazole and 1 l-(pyridin-2-ylthio)dioenzo[a,c]phenazine were synthesised too. Attempts to oxidise 1,3-dihydro-2H-4,9-diazanaphth[2,3-d]imidazole, prepared by condensation of 2,3-diaminoquinoxaline with cyclohexanone, to an analogue of the title system failed.

References (34)

  • HazeltonJ.C. et al.

    Tetrahedron

    (1995)
  • BussolottiD.L. et al.

    Tetrahidron Lett.

    (1991)
  • Van den BosscheH. et al.

    Adv. Pharmacol. Chemotherapy

    (1982)
  • GrimmettM.R.
  • IddonB.

    Bull. Soc. Chim. Belg.

    (1990)
  • JeffersonA.M. et al.

    J. Chem. Soc., Chem. Commun.

    (1977)
  • DaviesK.E. et al.

    J. Chem. Soc., Perkin Trans

    (1984)
  • GarnerR. et al.

    J. Chem. Soc. (C)

    (1970)
  • GorelikM.V. et al.

    J. Org. Chem. U.S.S.R., Engl. Transl.

    (1977)
  • SuschitzkyH. et al.

    J. Chem. Soc., Perkin Trans.

    (1988)
  • IddonB. et al.

    Synthesis

    (1988)
  • CadaA. et al.

    Helv. Chim. Acta

    (1990)
  • IddonB. et al.

    J. Chem, Soc., Perkin Trans

    (1992)
  • SchwochS. et al.

    Helv. Chim, Acta

    (1994)
  • GorelikM.V. et al.

    J. Org. Chem. U.S.S.R., Engl. Transl.

    (1978)
  • BrownH.D. et al.

    J. Am. Chem. Soc.

    (1961)
  • BurrowsR.B.

    Prog. Drug Res.

    (1973)
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    Part 9: Hazelton, J.C.; Iddon, B. ; Redhouse, A.D.; Suschitzky, H. Tetrahedron 1995, 51, 5597.

    2.

    For a review of earlier work and a preliminary announcement of this work see Iddon, B. Bull. Soc. Chim. Belg. 1990, 99, 673.

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