Ring Opening of 1,1’-Sulfonyl Bis-Aziridines Derived from L-Amino Acids and DFT Study of the Affinity Toward Different Nucleophiles

Title:Ring Opening of 1,1’-Sulfonyl Bis-Aziridines Derived from L-Amino Acids and DFT Study of the Affinity Toward Different Nucleophiles

Volume: 18 Issue: 12

Author(s): Nawel Khettache, Mohamed Dehamchia, Sihem Hessainia, Tahar Abbaz and Zine Régaïnia*

Affiliation:

• Laboratory of Applied Organic Chemistry (LCOA) Heterocyclic Chemistry Group, Department of Chemistry, Faculty of Sciences, Badji Mokhtar University, Annaba, PO Box 12,Algeria

Keywords: Bis-aziridines, thiadiazolidine, ring-opening, sulfamides, nucleophiles, density functional theory.

Abstract: We describe herein the ring-opening reaction of chiral 1,1’-sulfonyl bis-aziridines with various neutral and anionic nucleophiles including benzylamine, piperidine, acetate, allylthiolate, cyanide anion and sodium ethoxide. These reactions afforded bis-opened or/and mono-opened compounds via a regioselective attack on the non-substituted methylene of aziridine ring. The structures of the products were confirmed based on spectral analysis (IR, 1H NMR and 13C NMR). A theoretical study by density functional theory (DFT) was used to rationalize the region-selective ring-opening of starting bis-aziridines.

Cite this article as:

Khettache Nawel , Dehamchia Mohamed , Hessainia Sihem , Abbaz Tahar and Régaïnia Zine *, Ring Opening of 1,1’-Sulfonyl Bis-Aziridines Derived from L-Amino Acids and DFT Study of the Affinity Toward Different Nucleophiles, Letters in Organic Chemistry 2021; 18 (12) . https://dx.doi.org/10.2174/1570178618666210706112718