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Interaction of N,N-dimethylhydrazonomethyl and α-hydroxyketone groups in hetaryl analogs of unsymmetrical benzoins

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The reaction of phenylglyoxal hydrate with N,N-dimethylhydrazones of furfural and 1-methylpyrrole-2-carbaldehyde proceeds regioselectively at position 5 of the heterocycle. The hetaryl analogs of α-benzoins obtained are quantitatively isomerized into the isomeric β-benzoins. The N,N-dimethylhydrazonomethyl group, while activating the hetaryl residue, reduces the time for isomerization compared with unfunctionalized benzoins. The N, N-dimethylhydrazonomethyl group is readily transformed into an aldehyde or nitrile group and enters into a trans-hydrazonation reaction.

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Authors and Affiliations

  1. Dnepropetrovsk National University, Dnepropetrovsk, 49050, Ukraine

    S. P. Ivonin, A. V. Lapandin & V. G. Shtamburg

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  1. S. P. Ivonin
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  2. A. V. Lapandin
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  3. V. G. Shtamburg
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1805–1814, December, 2005.

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Ivonin, S.P., Lapandin, A.V. & Shtamburg, V.G. Interaction of N,N-dimethylhydrazonomethyl and α-hydroxyketone groups in hetaryl analogs of unsymmetrical benzoins. Chem Heterocycl Compd 41, 1484–1493 (2005). https://doi.org/10.1007/s10593-006-0025-2

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  • DOI: https://doi.org/10.1007/s10593-006-0025-2

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