New Chiral Aminoamidoximes: Syntheses and Investigation of Heterocyclic Compounds

Abstract

New chiral aminoamidoximes were prepared from (L)-proline, (L)-alanine, and (L)-isoleucine by treatment of the corresponding aminonitriles with hydroxylamine in the presence of triethylamine. The intramolecular cyclization with α-bromoacid chlorides and aldehydes was investigated to give new 1,2,4-oxadiazin-6-ones and 1,2,4-oxadiazoles, respectively. These compounds were likely to undergo an intermolecular cyclization through oxygen and nitrogen. However, intramolecular cyclization through two nitrogens did not occur even after changing reaction conditions.

GRAPHICAL ABSTRACT

Keywords:

• Aminoamidoximes
• intramolecular cyclization
• 1,2,4-oxadiazin-6-ones
• 1,2,4-oxadiazoles

ACKNOWLEDGMENT

The authors thank the DGRS (Direction Générale de la Recherche Scientifique) of the Tunisian Ministry of Higher Education and Scientific Research for the financial support of this research.