Synthesis of 3-hydrazino-6-tert-butyl-1,2,4-triazolo[3,4-c]-1,2,4-triazin-5-one

3-Hydrazino-6-tert-butyl-1,2,4-triazolo[3,4,c]-1,2,4-triazin-5-one was synthesized by the reaction of a substituted 4-(N,N-dimethylcarbamoyl)-3-thioxo-1,2,4-triazine with hydrazine. The spectral characteristics and the proposed reaction mechanism are discussed.The Sumy State University, Sumy 244007. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1258–1260, September, 1994. Original article submitted September 14, 1994.     

Heterocyclization of 6-tert-Butyl-3-hydrazino-2,5-dihydro-1,2,4-triazin-5-one with Benzoyl Chloride and Formic Acid

Reaction of 6-tert-butyl-3-hydrazino-2,5-dihydro-1,2,4-triazin-5-one with excess benzoyl chloride or formic acid afforded 6-tert-butyl-[1,2,4]triazolo[4,3-b][1,2,4]triazin-7(8H)-ones.     

Synthesis of 6-Hydroxy-2-methyl-3-thioxo-2H-1,2,4-triazin-5-one

The title compound has been prepared in three steps from 2-methylthiosemicarbazide following acylation, cyclisation and cation exchange chromatography. It was fully characterised by the usual spectroscopic means as well as by ¹⁵N nmr spectroscopy and X-ray crystallographic analysis.     

The Reactions of 6-(tert-Butyl)-3-hydrazino-1,2,4-triazin-5(2H)-one with Carbonyl Compounds

The reaction of 6-(tert-butyl)-3-hydrazino-1,2,4-triazin-5(2H)-one with acetone and benzaldehyde yields the corresponding hydrazones. In the presence of thionyl chloride the benzaldehyde hydrazone is converted to 3-(tert-butyl)-6-phenyl-1,2,4-triazolo[4,3-b]-1,2,4-triazin-2(1H)-one and this can also be formed via the acylation of the starting hydrazinotriazinone using benzoyl chloride.     

Structure of 4-amino-6- tert-Butyl-3-methylthio- 1,2,4-triazin-5-one

Journal of Structural Chemistry -     

The behavior of 6-p-chlorostyryl-3-thioxo-1,2,4-triazin-5-one toward phenylmagnesium bromide

The action of phenylmagnesium bromide on 6-p-chlorostyryl-3-thioxo-1,2,4-triazin-5-one ( 1 ) was studied whereby a mixture of seven products was obtained. These were separated and characterised, and a reasonable mechanism for their formation is presented and discussed.     

Efficient synthesis of 5-substituted-4,5-dihydro-1,2,4-triazin-6-ones and 5-substituted-1,2,4-triazin-6-ones

Treatment of methyl α-(dimethylarninomethyleneamino)carboxylates 1 (from α-amino acids and dimethylformamide dimethylacetal) with hydrazine gives 5-substituted-4,5-dihydro-1,2,4-triazin-6-ones 2 , which are smoothly dehydrogenated to 5-substituted-1,2,4-triazin-6-ones 3 with potassium permanganate in acetone/acetic acid.     

The most stable tautomer of 3-amino-1,2,4-triazin-5-one and its structural geometry

With the purpose of finding predominant tautomer among five possible isomers of 3-amino-1,2,4-triazin-5-one and to refine some unreasonable structural parameters previously reported from X-ray diffraction measurements, a series of ab initio calculations were carried out. In agreement with previous results, our calculations show that 3-amino-1,2,4-triazin-5(2H)-one tautomer is the most stable one. Concerning the predominant tautomer, comparisons were made between structural parameters calculated and those obtained by X-ray crystallographic analysis. The structural geometry of the main skeleton of the molecule calculated by the B3LYP/6-311++G** density functional method are generally in good agreement with the experimental values, and those predicted by Pauling's method. Bond distance values calculated are in excellent agreement with the conventionally accepted bond lengths in similar molecules. All bond distances, bond angles, dihedral angles, dipole moments and rotational constants are presented.     

5-苄基-4-氨基-3-巯基-1,2,4-三唑席夫碱合成与生物活性研究

为进一步研究三唑席夫碱化合物的合成与性质,以熔融法合成中间体5-苄基-4-氨基-3-巯基-1,2,4-三唑,再与取代醛在冰醋酸催化下回流反应合成了6个1,2,4-三唑席夫碱化合物,其结构通过元素分析,红外光谱,核磁共振氢谱进行了表征。生物测试结果表明,合成的三唑席夫碱化合物对烟草赤星病、马铃薯干腐病、小麦赤霉病、番茄早疫病、西瓜枯萎病5种植物病原菌具有较好的抑菌活性。     

Heteroannulation Through Palladium Catalysis: A Novel Cyclization Leading to Regioselective Synthesis of 3-Substituted Thiazolo[3,2-c]1,2,4-triazin-5-ones

A convenient, general, and one-pot synthesis of substituted thiazolo[2,3-c]1,2,4-triazinone from 3-propargylmercapto-1,2,4-triazin-5-one and aromatic iodide via palladium catalysis is described.     

Synthesis of 4-Amino-6-phenyl-3-thioxo-2,3-dihydro-1,2,4-triazine-5(4H)-one

Russian Journal of General Chemistry -     

Reaction of 3-Amino-5H- and 3-Amino-5-sulfanyl-1,2,4-triazoles with 1,2,4-Triazine-5-carbonitriles

Russian Journal of Organic Chemistry - 1,2,4-Triazines with an unsubstituted (1,2,4-triazol-3-yl)amine residue in the C5 position were synthesized by the solvent-free ipso-amination reaction...     

Preparation and Structure Characterization of 4-Amino-1,2,4-triazol-5-one Hydrate

4-Amino-1,2,4-triazol-5-one hydrate (ATO·H₂O) was prepared and its structure was analyzed by four-circle diffraction measurement. The obtained results show that the crystal belongs to the triclinic crystal system, space group P 1 with crystal parameters a = 6.432(1), b = 6.551(1), c = 6.740(1) ; = 68.04(1), = 82.18(1), = 81.90(1)°, V = 259.7(7) ³; Z = 2; Dc = 1.510 g/cm³; = 0.131 mm^-1; F(000) = 124. ATO·H₂O was characterized by FT-IR analysis, X-ray diffraction analysis, and single crystal diffraction analysis.