ChemInform Abstract: An Efficient Route to 1,3,5‐Triazido‐2,4,6‐tricyanobenzene.

Abstract

Benzonitriles and organic azides are of particular importance as components of dyes, herbicides, natural products, and drugs [1 – 6]. For example, it is possible to convert the nitrile group into a variety of other functional groups. Therefore benzonitriles are important intermediates for the synthesis of biologically important structures such as benzoic acid derivatives, benzyl amines, benzyl amides, and heterocyclic compounds. Due to the diverse applications of benzonitrile numerous synthetic possibilities have been developed. In particular, the Rosenmund-von-Braun reaction [7] (reaction of aryl halides with copper(I) cyanide) and the Sandmeyer reaction [8] (reaction of arene-diazonium salts with copper(I) cyanide) are used. The problem of both methods is the formation of stoichiometric amounts of heavy metal salts. Therefore, today aryl cyanides are produced primarily by the ammoxidation of the corresponding toluenes [9, 10]. This process requires harsh reaction conditions and shows a lack of tolerance of other functional groups. Another way to generate the nitrile group is the stepwise construction of a CN moiety by application of a series of classical organic synthesis steps as shown in Scheme 1. Here we report on the stepwise synthesis and full characterization of binary 1,3,5-triazido-2,4,6tricyanobenzene. Results and Discussion