Spectral studies of products of reaction between phosphorylacetaldehyde thiosemicarbazones and bromoacetal

Abstract

We have obtained thiazoline hydrobromides by reacting unsubstituted thiosemicarbazones of phosphorylacetaldehydes with bromoacetal. These thiazoline hydrobromides have the structure of the azine of phosphorylacetaldehyde and 1,3-thiazoln-2-one in the crystal phase. Their dissolution is accompanied by thiazoline-thiazole tautomeric conversion to the hydrobromide of phosphorylacetaladehyde thiazolylhydrazone. Reaction of the 2-methyl-substituted phosphorylacetaldehyde thiosemicarbazone with bromoacetal leads to the hydrobromide of phosphorylacetaldehyde N-methyl-N-2-(1,3-thiazolyl)hydrazone, the thiazole structure of the heterocycle of this compound is also retained when it is dissolved, due to the impossibility of tautomeric conversions due to the structural features. In all cases, salt formation occurs at the endocyclic nitrogen atom. The conversion of salt-like compounds to free bases does not lead to a change in the thiazole structure of the heterocycle.

How to Cite
Pavlov, V. A.; Smith, J. A. S. Chem. Heterocycl. Compd. 1996, 32, 721. [Khim. Geterotsikl. Soedin. 1996, 837.]

For this article in the English edition, see DOI https://doi.org/10.1007/BF01164874