8-(Pyrimidin-2-yl)-1,2,3,4,5,6,7,8-heptathiazocane

Vladimir A Ogurtsov,Oleg A Rakitin

doi:10.3390/m1091

Abstract

Heptasulfur imides substituted by hereterocycle may be of interest as biologically active compounds. In this communication, the reaction of pyrimidin-2-amine 1 with disulfur dichloride was carefully investigated to give 8-(pyrimidin-2-yl)-1,2,3,4,5,6,7,8-heptathiazocane in good yield. The structure of the newly synthesized compound was established by means of elemental analysis, high resolution mass-spectrometry, 1H, 13C NMR and IR spectroscopy and mass-spectrometry.

Highlights

From cyclic sulfur imides with the general formula S8-x(NH)x heptasulfur imide (S7NH) is available and the most investigated representative of this class [1]
It is known that disulfur dichloride is an important reagent in the synthesis of heterocycles with various numbers of sulfur atoms [7,8,9]
In order to develop the synthesis of heptasulfur imides substituted by hereterocycle, which may be of interest as biologically active compounds, the reaction of pyrimidin-2-amine 1 with disulfur dichloride in the presence of a base was examined (Scheme 1)

Summary

Introduction

From cyclic sulfur imides with the general formula S8-x(NH)x heptasulfur imide (S7NH) is available and the most investigated representative of this class [1]. There is only one example of heterocyclic derivatives of heptasulfur imide; methyl 7-(1,2,3,4,5,6,7,8-heptathiazocan-8-yl)-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate was obtained in low (8%) yield in the reaction of the corresponding heterocyclic amine and disulfur dichloride [6]. We report the synthesis of previously unknown 8-(pyrimidin-2-yl)-1,2,3,4, 5,6,7,8-heptathiazocane and study of conditions of its formation.

Results

Conclusion