INTERACTION OF N,N-DIMETHYLHYDRAZONOMETHYL AND α-HYDROXYKETONE GROUPS IN HETARYL ANALOGS OF UNSYMMETRICAL BENZOINS

Authors

  • С. П. Ивонин Dnepropetrovsk National University, Dnepropetrovsk 49050
  • А. В. Лапандин Dnepropetrovsk National University, Dnepropetrovsk 49050
  • В. Г. Штамбург Dnepropetrovsk National University, Dnepropetrovsk 49050

DOI:

https://doi.org/10.1007/8111

Keywords:

benzoins, hydrazones, π-excess heterocycles, isomerization, electrophilic substitution

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.

How to Cite
Ivonin, S. P.; Lapandin, A. V.; Shtamburg, V. G.  Chem. Heterocycl. Compd. 2005, 41, 1484. [Khim. Geterotsikl. Soedin. 2005, 1805.]

For this article in the English edition, see DOI 10.1007/s10593-006-0025-2


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Published

2023-10-11

Issue

No. 12 (2005)

Section

Original Papers