v-Triazolines. Part II. Synthesis and reactions of 5-amino-4-aminomethyl-1-aryl-v-triazolines

Abstract

5-Amino-4-aminomethyl-1-aryl-v-triazolines are synthesized by treating aryl azides with acrylaldehyde and secondary amines. The triazolines readily react with strong bases yielding the corresponding triazoles. Acids act differently, depending on the kind of the amine residues. When these are strongly basic (aliphatic) the triazoline ring is cleaved with nitrogen evolution. Among the degradation products propane-1,2-dione is identified. When the amine residues are less basic (aromatic) the ring is not cleaved and both the corresponding 1-aryl-v-triazoles and 4-aminomethyl-1-aryl-v-triazoles are obtained. The mechanisms of these reactions are discussed.