TDAE strategy for the synthesis of 2,3-diaryl N-tosylaziridines

Omar Khoumeri; Cédric Spitz; Thierry Terme; Patrice Vanelle

doi:10.3390/molecules18077364

TDAE strategy for the synthesis of 2,3-diaryl N-tosylaziridines

Molecules. 2013 Jun 24;18(7):7364-75. doi: 10.3390/molecules18077364.

Authors

Omar Khoumeri¹, Cédric Spitz, Thierry Terme, Patrice Vanelle

Affiliation

¹ Laboratoire de Pharmaco-Chimie Radicalaire, Faculté de Pharmacie, Institut de Chimie Radicalaire ICR, Aix-Marseille Université, UMR CNRS 7273, 27 Boulevard Jean Moulin - CS 30064, 13385 Marseille Cedex 05, France.

Abstract

We report herein an original and rapid synthesis of 2,3-diaryl N-tosylaziridines by TDAE strategy starting from ortho- or para-nitro(dichloromethyl)benzene derivatives and N-tosylimines. A mixture of cis/trans isomers was isolated from 1-(dichloromethyl)-4-nitrobenzene, whereas only trans-aziridines were obtained from ortho-nitro derivatives.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Aziridines / chemical synthesis*
Aziridines / chemistry
Dimethylamines / chemical synthesis
Dimethylamines / chemistry*
Ethylenes / chemical synthesis
Ethylenes / chemistry*
Nitrobenzenes / chemical synthesis*
Nitrobenzenes / chemistry
Stereoisomerism

Substances

Aziridines
Dimethylamines
Ethylenes
Nitrobenzenes
nitrobenzene
tetrakis(dimethylamino)ethylene