Development of New Synthetic Methods of Heterocycles Using Chloramine-T as a Nitrogen Source

Abstract

We have exploited the novel strategies for construction of N-heterocycles using Chloramine-T as an N1 unit. Copper (I) chloride or iodine was found to be a good catalyst for aziridination of various alkenes with Chloramine-T. The combination of Chloramine-T and silver nitrate directly led to not only aziridines from alkenes including α, β-unsaturated carbonyl compounds but also bicyclic pyrrolidines from 1, 6-dienes. The synthesis of pyrrolidine derivatives was achieved efficiently and stereoselectively from alkenyl iodides and Chloramine-T, in which the iodo group of the substrates has multiple functions to perform the cyclization. Furthermore, organic-solvent-free aziridination of alkenes was developed by utilizing Chloramine-T-I2 system under phase-transfer catalyst conditions or under the reaction media of silica and water.