Convenient Synthesis of 1,2-Diamines from β-Chloro Amines: Precursors of New Substituted Piperazin-2-ones

Abstract

A practical synthesis of 1,2-diamines from β-chloro amines is reported. The reaction proceeds through the intermediacy of an aziridinium ion opening by amines. The conversion of these diamines into polysubstituted piperazinones is also investigated.

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GRAPHICAL ABSTRACT

Keywords:

• Aziridinium ion
• β-chloro amines
• 1,2-diamines
• piperazin-2-ones

ACKNOWLEDGMENT

We thank M. A. Sanhoury, member of the Royal Society of Chemistry (MRSC) of the Department of Chemistry, Faculty of Sciences of Tunis, for helpful discussions.

Notes

^a 4f–h were 1:1 mixtures of two diastereomers (α + β) derived from the 1:1 mixture of 3f–h.

^b Yields refer to chromatographically isolated pure compounds.

^a 5f and g were 1:1 mixtures of two diastereomers (α + β) derived from the 1:1 mixture of 4f and g.

^b Yields refer to chromatographically isolated pure compounds.