Chemistry of Heterocyclic Compounds

, Volume 22, Issue 5, pp 532–538 | Cite as

Reaction of 1-methyluracil with phenylbenzhydrazonoyl chloride

  • N. B. Chernyshova
  • V. N. Shibaev
Article
  • 39 Downloads

Abstract

The ambident anion of 1-methyluracil gives with phenylbenzyhydrazonoyl chloride, depending on the conditions, the N-acylation product (polar solvent, room temperature), or the O-acylation product (nonpolar solvent, heating), which rearranges to a cytosine derivative. Convenient methods have been developed for the preparation of 6-methyl-1,3-diphenyl-5,6-dihydro-5-oxopyrimido[4,3-c]triazolium chloride, a fluorescent derivative of 1-methyluracil, from the N-acylation product, and for the rapid base cleavage of the uracil ring under very mild conditions.

Keywords

Chloride Organic Chemistry Cytosine Triazolium Uracil 

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Copyright information

© Plenum Publishing Corporation 1986

Authors and Affiliations

  • N. B. Chernyshova
    • 1
  • V. N. Shibaev
    • 1
  1. 1.N. D. Zelinskii Institute of Organic ChemistryMoscow

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