Synthesis of compounds of the 1,2,4-aminotriazines series

Abstract

Thestreamlined synthesis of compounds with wide spectrum of essential properties is prospective lines of development of chemistry of nitrogen containing heterocyclic compounds. Triazines hold a specific place among the great variety of nitrogen containing heterocyclic compounds. Derivatives of unsymmetrical triazines demonstrate a large range of bioactive action, they were offered in the quality of herbicides, plant growth regulators, insecticides, antifungal, acaricide, pharmaceutical and veterinary preparations, stabilizer-antioxygen of polymers and also as corrosion inhibitor. Compounds of 1,2,4-triazinones series are widely reported in the publications, but unsymmetrical triazines particularly their acyl and amino derivatives haven’t been studied detailed. Especially there are not many articles about route for the synthesis of acyl and amino derivatives. Known methods of synthesis based on the hardly accessible materials. For this reason developing of new methods of unsymmetrical triazines synthesis on the base of available petrochemical raw materials and investigation of their properties and fields of their application are promising direction. The reactions of aminoguanidine and hydrazine hydrate with carboxylic acids derivative, that led to 1,2,4-triazines with the amino group in the different position were studied. 3-Amino-1,2,5,6-tetrahydro-1,2,4-trizain-6-on obtained by interaction of chloracetylchloride and unsubstituted aminoguanidine. 4-amino-1,4,5,6-tetrahydro-1,2,4-triazin-5-on forms in the reaction of monochloracetic acid with hydrazine hydrate. 4-Amino-1,2,5,6-tetrahydro-1,2,4-trizain-5,6-dion was synthesized from diethyl oxalate, hydrazine hydrate and formic acid. On the base of synthesized amino-triazines and isobutyryl chloride corresponding amides were obtained. Physico-chemical constants of obtained compounds are shown. It is determined that data of elemental analysis of obtained compounds correspond to theoretically calculated values in range of standard deviation.