Synthesis, solvatochromism and crystal structure of 5-Methoxy-5,6-diphenyl-4,5-dihydro-2H −1,2,4-triazine-3-thione

Abstract

BackgroundFor the development of properties in molecular crystals, such as electrical conductivities, magnetic properties, or non-linear optical properties, not only the electronic properties of molecules themselves matter, but also the molecular arrangements in the crystals are very important. Therefore, the design of the crystal structures and the control of molecular arrangements have attracted much attention in recent years. Among various ligands, triazine moieties have been especially interesting because of their biological, pharmacological and medicinal properties.ResultsCrystal structure of 5-Methoxy-5,6-diphenyl-4,5-dihydro-2H-1,2,4-triazine-3-thione is Monoclinic, which consists of space group P21/c with a = 9.699(1), b = 8.500(1), c = 18.044(2) Å, β = 101.290(7)° and Z = 4, R1 = 0.0371 and wR2 = 0.1008 with 2456 reflections (I > 2σ(I)). Intermolecular H bonds between NH groups are acting as donors and S atoms as acceptors. There are also shorted face-to-face as well as edge to face π-π stacking interactions between the parallel aromatic rings. The behavior of solvatochromic of the mentioned compound that involved interhydrogen bonding was investigated by studying its electronic absorption spectra in pure organic solvents of different characters.ConclusionsThe crystal structure of C16H15N3OS, shows the expected face-to-face π-π stacking interactions between aromatic rings of the neighbor chains in this compound. The centroid–centroid distance between the aromatic rings is 3.325 Å. It was found that the monomer of the ligand 5-Methoxy-5,6-diphenyl-4,5-dihydro-2H-1,2,4-triazine-3-thione, further extends into 3D networks via hydrogen bonding and pi-pi stacking interactions. The solvatochromic behavior of the title compound was also investigated by studying its spectra in a selection of different organic solvents. While progressing from the non-polar solvent to the polar one, the main intense band at 310 nm, which is due to the π–π* transition, was red shifted by 13 nm. Thus, the title compound showed positive solvatochromic behavior.

Heterocyclization of 3-Propargylsulfanyl-5 Phenyl-1,2,4-Triazine: Tandem Reactions With Bromine Leading to New Derivatives of 7 Phenyl[1,3]thiazolo[3,2-B][1,2,4]triazinium

“…1). The Z-configuration of the exocyclic double bond is corroborated by the spin-spin coupling between the H-2 and H-1' protons, 4 J HH = 3.2 Hz, as well as by the cross peak between these protons in the 2D NOESY spectrum. When triiodide 3 is treated by sodium iodide in acetone, (3Z)-3-iodomethylene-7-phenyl-2,3dihydro [1,3] 5) is formed, which precipitates from the reaction mixture as a dark red sediment.…”

“…It is well known that derivatives of 1,2,4triazine-3-thione exhibit pesticide activity [1], as well as anticancer [2], psychotropic [3], and antiviral activity [4]. Annelated derivatives of triazines offer prom-ise in the field of drug development [5][6][7][8][9], in particular for neurodegenerative diseases [10].…”

“…In the literature [16] there are data for alkylation in tetrahydrofuran of 5-phenyl-2,3-dihydro-1,2,4triazine-3-thione (1) by benzyl, butenyl, and butynyl halides, proceeding at the sulfur atom. Heterocyclization of 3-allylsulfanyl- [17], 3-cinnamylsulfanyl-5phenyl-1,2,4-triazine [18], as well as 3-alkenylsulfanyl- [19] and 3-propargylsulfanyl-5H- [1,2,4]triazino [5,6b]indoles [20] under the action of halogens progresses with participation of the N-2 nitrogen atom of the triazine cycle producing thiazolo(thiazino) [3,2-b][1,2,4]triazine systems. In the present study in an effort to obtain new annulated heterocyclic systems 3-propargylsulfanyl-5-phenyl-1,2,4-triazine (2) has been synthesized for the first time, and its interaction with halogens has been investigated.…”

Alkylation of 5-phenyl-6R-2Н-1,2,4-triazine-3-thione and Heterocyclization of 1-(4-Bromophenyl)-2-(5-phenyl-6R-1,2,4-triazine-3-ylsulfanyl)ethanones.

“…К раствору 0,289 г (1,53 ммоль) 5-фенил-1,2,4-триазин-3-тиона в 10 мл ацетона добавляли 1,5 мл Et 3 N и 0,424 мл (1,53 Обсуждение результатов 5,6-Дифенил-2Н-1,2,4-триазин-3-тион (1a) был получен ранее взаимодействием бензила с тиосемикарбазидом в этаноле в присутствии карбоната калия с выходом 80 % [25]. Отметим, что взаимодействие бензила с тиосемикарбазидом в этаноле в присутствии концентрированной соляной кислоты приводит к синтезу 5-метокси-5,6-дифенил-4,5-дигидро-2Н-1,2,4-триазина, структура которого доказана методом РСА [26], в то время как аналогичное взаимодействие при 120 °С и микроволновом облучении в течение 10 мин уже даёт соединение 1 [7]. К образованию гидрированного 5,6-дифенил-триазинтиона приводит конденсация бензила с тиосемикарбазидом в метаноле в присутствии концентрированной соляной кислоты и NaBH 4 [27].…”

Efeito citotóxico contra células de câncer de pulmão de novos complexos de rutênio(II) contendo ligantes bifosfínicos, tiossemicarbazonas e semicarbazonas

“…complexos 95,116. Para o ligante Btsc essa banda foi observada em 323 nm, já para o ligante Bsc em 280 nm.…”