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Derivatives of α,β-dehydro amino acids: III. Reaction of 4-arylmethylidene-4,5-dihydro-1,3-oxazol-5-ones with hexamethyldisilazane

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Abstract

4-Arylmethylidene-4,5-dihydro-1,3-oxazol-5-ones reacted with hexamethyldisilazane in ethyl acetate, acetonitrile, or DMF at room temperature to give mainly 2-acylamino-3-arylmethylideneprop-2-enamides, whereas in boiling DMF the corresponding 4-arylmethylidene-4,5-dihydro-1H-imidazol-5-ones were formed. The reaction of 2-benzoylamino-3-phenylprop-2-enamide with hexamethyldisilazane also led to the formation of 4-benzylidene-2-phenyl-4,5-dihydro-1H-imidazol-5-one, while its reaction with chlorotrimethylsilane afforded either a 1:1 mixture of 4-benzylidene-2-phenyl-4,5-dihydro-1,3-oxazol-5-one and 4-benzylidene-2-phenyl-4,5-dihydro-1H-imidazol-5-one or only the latter, depending on the solvent.

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Authors and Affiliations

  1. Institute of Fine Organic Chemistry, National Academy of Sciences of Armenia, pr. Azatutyana 26, Erevan, 375014, Armenia

    V. O. Topuzyan, L. G. Arutyunyan & A. A. Oganesyan

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  1. V. O. Topuzyan
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  2. L. G. Arutyunyan
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  3. A. A. Oganesyan
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Additional information

Original Russian Text © V.O. Topuzyan, L.G. Arutyunyan, A.A. Oganesyan, 2007, published in Zhurnal Organicheskoi Khimii, 2007, Vol. 43, No. 6, pp. 870–873.

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Topuzyan, V.O., Arutyunyan, L.G. & Oganesyan, A.A. Derivatives of α,β-dehydro amino acids: III. Reaction of 4-arylmethylidene-4,5-dihydro-1,3-oxazol-5-ones with hexamethyldisilazane. Russ J Org Chem 43, 868–871 (2007). https://doi.org/10.1134/S1070428007060127

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  • DOI: https://doi.org/10.1134/S1070428007060127

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