Intramolecular catalysis of aminolysis of phosphorus heterocycles incorporating an α-aminoamide moiety. III. Synthesis of 2-oxo or 2-thioxo 1,3-disulfonyl-1,3,2-diazaphospholidines and reactions with amines and alcohols

✍ Scribed by Frédéric J. M. Dujols; Michel E. Mulliez

• Publisher: Journal of Heterocyclic Chemistry
• Year: 2001
• Tongue: English
• Weight: 78 KB
• Volume: 38
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.5570380227

✦ Synopsis

Abstract

A series of 2‐oxo or 2‐thioxo 1,3‐disulfonyl‐1,3,2‐diazaphospholidines 4was prepared by condensation of phosphonyl dichlorides 2 with bis‐N,N'‐sulfonylethylenediamines 1 in pyridine. Complete aminolysis or alcoholysis of heterocycles 4 took place with regeneration of sulfonyldiamines 1. These reactions are very sensitive to steric hindrance, and hydrolysis is generally favoured over aminolysis. The results are discussed in terms of mechanisms of phosphorylation.