The Studies on the Synthesizing Dibenzodiazocinediimine via Constructing an Eight-Membered Ring

A one-step and facile strategy to synthesize dibenzo[b,f][1,5]diazocine-6,12(5H,11H)-diimine and its analogs via the construction of an eight-membered ring has been established using o-aminobenzonitrile or o-phenylenediamine/phthalonitrile derivatives as raw materials. Twelve compounds, including 9 new compounds, have been synthesized in yields ranging from 62-95%. Five new compounds of 5,12-dihydrodibenzo[b,f][1,4]diazocine-6,11-diimine derivatives have also been synthesized in yields of 35-52%. Furthermore, the reaction between arylnitriles and various amines was also efficiently established under similar reaction conditions. Finally, a reasonable mechanism involving sodium as a proper base to initiate the cyclization process was proposed.