Continuous flow system for biphasic synthesis of gem‐dichloroaziridine derivatives

Abstract

gem‐Dichloroaziridines are essential building blocks in the synthesis of biologically and pharmacologically active compounds. We developed a continuous flow biphasic system to overcome the limitation of conventional batch systems, in which dichlorocarbene generated from the reaction of chloroform and a NaOH combined with azomethines to generate gem‐dichloroaziridine derivatives in good yields. Then a two‐step one‐flow process was designed with the addition of flow synthesis of N‐benzylideneaniline. This process is also advantageous in protecting the researcher from irritating odors and harmful reactants and intermediates.

Advances in the Continuous Flow Synthesis of 3‐ and 4‐Membered Ring Systems

“…An analogous reaction has also been demonstrated by Park and colleagues when generating gem-dichloroaziridines from imines in continuous flow. [12] Similar reactivity is observed when alkenes are treated with metal carbenoids, such as in the Simmons-Smith reaction. The Simmons-Smith reaction involves formation of a zinc carbenoid species by reacting diiodomethane with mixtures of zinc and copper.…”