Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles

This method can help to answer key questions in the field of bicyclic aziridinium ion chemistry for the synthesis of various various azaheterocycles including bipyridine and azepine ring systems. The main advantage of this technique is that the synthesis of kai-dal bipyridines and azepine core present in various natural products is achieved in a straight-forward manner. First, add 100 milligrams of the alcohol, 140 microliters of triethylamine, and a magnetic stir bar into an oven dried 25 milliliter two-neck round bottom flask under nitrogen atmosphere.

Using an airtight syringe, add 5 milliliters of anhydrous dichloromethane to the reaction flask. Cool the reaction mixture to 0 degrees Celsius using an ice water bath and stir the mixture for 5 minutes. Next, add 164 milligrams of p-toluenesulfonic anhydride to the reaction mixture and stir for another 45 minutes.