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Synthesis of 2,5-diaryl-1,3-oxazoles containing a carbamate group

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Abstract

Acetophenones containing a methoxycarbonylamino group in position 2, 3, or 4 of the aromatic ring reacted with phenylglycine in the presence of 2 equiv of iodine and 0.5 equiv of sulfanilic acid in DMSO at 100°C for 6 h to give methyl [2(3,4)-(2-phenyl-1,3-oxazol-5-yl)phenyl]carbamates. The reaction was presumed to involve intermediate formation of methyl [(iodoacetyl)phenyl]carbamate. This was confirmed by the isolation of methyl [2-(iodoacetyl)phenyl]carbamate in the reaction of methyl (2-acetylphenyl)carbamate with iodine in glacial acetic acid and its subsequent transformation to methyl [2-(2-phenyl-1,3-oxazol-5-yl)-phenyl]carbamate.

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Authors and Affiliations

  1. Astrakhan State University, pl. Shaumyana 1, Astrakhan, 414000, Russia

    A. V. Velikorodov, E. A. Shustova & S. B. Nosachev

Authors
  1. A. V. Velikorodov
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  2. E. A. Shustova
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  3. S. B. Nosachev
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Correspondence to A. V. Velikorodov.

Additional information

Original Russian Text © A.V. Velikorodov, E.A. Shustova, S.B. Nosachev, 2017, published in Zhurnal Organicheskoi Khimii, 2017, Vol. 53, No. 12, pp. 1821–1823.

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Velikorodov, A.V., Shustova, E.A. & Nosachev, S.B. Synthesis of 2,5-diaryl-1,3-oxazoles containing a carbamate group. Russ J Org Chem 53, 1857–1859 (2017). https://doi.org/10.1134/S1070428017120120

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  • DOI: https://doi.org/10.1134/S1070428017120120

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