sym-triazine derivatives. 9. Reaction of sym-triazines containing trichloromethyl and ethoxycarbonyl groups with phenylhydrazine

✍ Scribed by N. V. Alekseeva; K. F. Turchin; O. S. Anisimova; Yu. N. Sheinker; L. N. Yakhontov

• Publisher: Springer US
• Year: 1990
• Tongue: English
• Weight: 710 KB
• Volume: 26
• Category: Article
• ISSN: 0009-3122
• DOI: 10.1007/bf00473967

✦ Synopsis

Using the example of the reaction of l,3,5-triazines simultaneously containing trichloromethyl and ethoxycarbonyl substituents with phenylhydrazine, it was shown that the presence of even one ester group leads to ring transformation. Depending on the number of the ester groups in the initial 1,3,5-triazine, the reaction products are either 12,4-triazole or 12,4-triazine derivatives.

It was previously shown that in the reaction of 2,4,6-1xiethoxycarbonyl-l,3,5-aiazine (I) with phenylhydrazine (II) the product is 5-amino-6-oxo-l-phenyl-3-ethoxycarbonyl-l,6-dihydro-l,2,4-triazine (iII, Scheme 1 on page 1376) [1],

It was of interest to study the reaction of hydrazine II with 1,3,5-a'iazines also containing other substituents besides the ethoxycarbonyl groups. The most easily accessible were 2,4,6-tris(trichloromethyl)-, 2,4-bis(trichloromethyl)-6-ethoxycarbonyl-and 2-trichloromethyl-4,6-bis(ethoxycarbonyl)-l,3,5-triazines (IV, V, and VI) which were obtained by joint trimerization of trichloroacetonitrile and ethyl cyanoformate by a method described in [2]. *For Communication 8, see [1].