Synthesis and optical properties of some 3,4-(ethylenedioxythiophen-2-yl)-1,2,4-triazine derivatives

Branowska, Danuta; Olender, Ewa; Świętochowska, Monika; Karczmarzyk, Zbigniew; Wysocki, Waldemar; Cichosz, Iwona; Woźna, Agnieszka; Urbańczyk‐Lipkowska, Zofia; Kalicki, Przemysław; Gil, Michał

doi:10.1016/j.tet.2016.12.030

Cited by 6 publications

(2 citation statements)

References 22 publications

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“…The thiomethyl group is a versatile moiety for coupling reactions. In triazines, the thiomethyl group may be easily substituted with aryl boronic acids [ 84 , 85 ] or trialkyl(aryl)stannanes [ 86 ] using Liebeskind–Srogl coupling [ 87 ]. To demonstrate the synthetic potential of benzofuro-annulated triazines, we performed the substitution of the thiomethyl group with an aryl substituent.…”

Section: Resultsmentioning

confidence: 99%

MnO2-Mediated Oxidative Cyclization of “Formal” Schiff’s Bases: Easy Access to Diverse Naphthofuro-Annulated Triazines

et al. 2022

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A different type of MnO2-induced oxidative cyclization of dihydrotriazines has been developed. These dihydrotriazines are considered as a “formal” Schiff’s base. This method provided easy access to naphthofuro-fused triazine via the C-C/C-O oxidative coupling reaction. The reaction sequence comprised the nucleophilic addition of 2-naphthol or phenol to 1,2,4-triazine, followed by oxidative cyclization. The scope and limitations of this novel coupling reaction have been investigated. Further application of the synthesized compound has been demonstrated by synthesizing carbazole-substituted benzofuro-fused triazines. The scalability of the reaction was demonstrated at a 40 mmol load. The mechanistic study strongly suggests that this reaction proceeds through the formation of an O-coordinated manganese complex.

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Section: Resultsmentioning

confidence: 99%

MnO2-Mediated Oxidative Cyclization of “Formal” Schiff’s Bases: Easy Access to Diverse Naphthofuro-Annulated Triazines

et al. 2022

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“…Annelated derivatives of triazines offer prom-ise in the field of drug development [5][6][7][8][9], in particular for neurodegenerative diseases [10]. Besides, 3-methylsulfanyl-1,2,4-triazine has been used as a base for oligomers with optoelectronic properties [11]. Derivatives of 1,2,4-triazine are used as synthons in synthesis of various pyridines according to the Diels-Alder reaction [12][13][14][15].…”

Section: Introductionmentioning

confidence: 99%

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

Rybakova

Kim

Данилина

et al. 2020

IVKKT

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Derivatives of 1,2,4-triazine-3-thione exhibit biological activity in a wide range. They have optoelectronic properties and can be used as synthons in synthesis of various pyridines by the Diels-Alder reaction. 1,2,4-Triazines are of the greatest interest, for organic synthesis in particular. In the present study we have established that the interaction of 3-propargylsulfanyl-5-phenyl-1,2,4-triazine, obtained by alkylation of 5-phenyl-2,3-dihydro-1,2,4-triazine-3-thione with 3-bromopropyne in acetone in the presence of triethylamine, with halogens leads to annelation of thiazole cycle. At that, [1,3]thiazolo[3,2-b][1,2,4]triazinium systems contain either endo- or exocyclic double bond in their structure, depending on the halogen type. By way of example, iodine acting on propargyl sulfide forms a dark precipitate of (3Z)-3-iodomethylene-7-phenyl-2,3-dihydro-[1,3]thiazolo[3,2-b][1,2,4]triazinium triiodide, the structure of which has been confirmed by 1H and 13C NMR spectroscopy, including two-dimensional 2D 1H-13C HSQC, HMBC and 1H-1H NOESY experiments. Treatment of the obtained triiodide by sodium iodide in acetone leads to synthesis of the corresponding monoiodide, which precipitates from the reaction mixture as a dark red precipitate. Reaction with bromine, as distinct from heterocyclization under iodine action, comprises an unusual cascade reaction including the stages of electrophile heterocyclization, bromine addition, and hydrogen bromide elimination, which leads to formation of 3-dibromomethyl-7-phenyl[1,3]thiazolo[3,2-b][1,2,4]triazinium bromide. It should be pointed out that the identifying feature of 3-propargylsulfanyl-5-phenyl-1,2,4-triazine heterocyclization under iodine and bromine action is the signal bias of the aromatic proton in a triazine ring towards weak field in the 1H NMR spectrum of the reaction products. This is presumably associated with formation of the positively charged nitrogen atom.

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1,2,4-Triazines and Their Benzo Derivatives

Иванов¹

2022

Comprehensive Heterocyclic Chemistry IV

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Synthesis and optical properties of some 3,4-(ethylenedioxythiophen-2-yl)-1,2,4-triazine derivatives

Cited by 6 publications

References 22 publications

MnO2-Mediated Oxidative Cyclization of “Formal” Schiff’s Bases: Easy Access to Diverse Naphthofuro-Annulated Triazines

MnO2-Mediated Oxidative Cyclization of “Formal” Schiff’s Bases: Easy Access to Diverse Naphthofuro-Annulated Triazines

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

1,2,4-Triazines and Their Benzo Derivatives

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