Use of dilithio-tosylmethyl isocyanide in the synthesis of oxazoles and imidazoles

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Abstract

Dilithio-tosylmethyl isocyanide (2) reacts with the carbonyl of unsaturated esters to form oxazoles, unlike tosylmethyl isocyano monoanion which gives pyrroles by reaction with the conjugated carbon-carbon double bonds. Reaction of 2 with carbon-nitrogen multiple bonds leads to imidazoles, an example of which is the one-step synthesis of imidazo[5,1-a]isoquinoline from isoquinoline. From 2 and pyridine-N-oxide or pyridazine-N-oxide unsaturated ring opened products are obtained.

References (14)

  • A.M. van Leusen
    (1980)
  • S.P.J.M. van Nispen

    Ph.D. thesis

    (1980)
  • D. van Leusen, unpublished...
  • O. Possel et al.

    Heterocycles

    (1977)
    (b)Methyl cinnamate and TosMIC with NaH in DMSO-Et2O give methyl 4-phenylpyrrole-3-carboxylate in 70% yield: A.M. van...
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Chemistry of Sulfonylmethyl Isocyanides 21; for part 20 see: A.M. van Leusen and P.G. Oomkes, Synth. Comm., 10, 399 (1980).

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