Aminoazines are interesting intermediates in the preparation of 1,2,4-triazoles 1,2 and imidazoles. 3 1-Amino-1,4-diphenyl-2,3diazabutadiene (3) was first made in 1914 by Stollé, 4 from the reaction of the corresponding chloro-azine with ammonia. 3,5-Diphenyltriazole and diphenyltetrazine were formed as by-products. In 1971, Taylor and co-workers repeated this reaction and obtained the amino-azine (3) in 38% yield. 1,4-Diamino-1,4diphenyl-2,3-diazabutadiene, 3,5-diphenyltriazole, and diphenyltetrazine were also obtained as by-products. 1 Another route to amino-azine (3) was reported by van der Burg, 5 who claimed that the reaction of amidrazones with benzaldehyde would give their N 1 -benzylidene derivatives, which are amino-azines. However, conflicting reports have appeared in the literature concerning the products formed in such reactions.Taylor 6 and Case 7 came to the same conclusion as van der Berg, and stated that the reaction of amidrazones with monocarbonyl compounds would give their aryl or alkylidene derivatives. On the other hand, Case reported the formation of 1,2,4-triazolines rather than amino-azines. [8][9][10] Zelenin claimed the formation of both amino-azines and triazolines. 11
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