Synthesis of 2-(Polyhydroxy)alkyl- and 2-(6-Adenosinyl)benzisoselenazol-3(2H)-ones

Abstract

A convenient method for synthesis of benzisoselenazol-3(2H)-ones substituted on the nitrogen atom with (polyhydroxy)alkyl or adenosinyl group is presented. It is based on the tandem acylation–selenenylation of primary amino group in aminopolyols or adenosine with 2-(chloroseleno)benzoyl chloride. The process is selective because oxygen nucleophiles (hydroxy groups) remained unreactive in the reaction conditions.

Keywords:

• 2-(chloroseleno)benzoyl chloride
• Benzisoselenazol-3(2H)-ones
• Nucleosides
• Polyols
• Selenium compounds

Acknowledgment

This work was supported by the Polish State Committee for scientific research (Grant No. 3 T09A 097 17).