Polyfunctional aliphatic compounds VI. The cyclization of dinitriles to benzazepines

Publisher Website
Google Scholar
Abstract
The action of hydrogen bromide or iodide on aryl‐o‐diacetonitriles has been studied and found to give condensed azepine derivatives. This constitutes a new and interesting synthesis of seven‐membered ring nitrogen heterocycles. The structure of the parent substance has been shown by physical and chemical means to be 2‐amino‐4‐halo‐1H‐3‐benzazepine. Several related compounds have been prepared and assigned similar structures by analogy. A number of reactions of 2‐amino‐4‐bromo‐1H‐3‐benzazepine (III) have been examined. It is concluded that the reactivity of the bromo group is similar to that of 2‐bromopyridine. In its reactions, 2‐amino‐1H‐3‐benzazepine not only has some of the character of 2‐aminopyridine but resembles the simple amidines also.