Tribromoisocyanuric acid as an alternative oxidant in the synthesis of 2-amino-1,3,4-oxadiazoles from 1-acylthiosemicarbazides

Crispim-Neto, Jaime; Mattos, Marcio C. S. de

doi:10.1016/j.tetlet.2023.154494

Cited by 5 publications

(1 citation statement)

References 48 publications

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“…В даній роботі наведено синтез алільних тіоетерів 5-нітрофеніл-1,3,4оксадіазолу реакцією алкілування відповідних тіонів аліл бромідом в спиртово-лужному середовищі. Такі тіоетери досліджувалися в реакціях з фенілселентригалогенідами, в результаті чого синтезовано галогеніди оксадіазоло [2,3-d] [1,3,4]тіаселеназинію. Нами досліджено взаємодію телуровмісного аналогу -п-метоксифенілтелуртрихлориду з алільними тіоетерами 5-нітрофеніл-1,3,4-оксадіазолу.…”

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COMPLEXES OF p-METHOXYPHENYLTELLURIUM TRICHLORIDE WITH ALLYL THIOETHERS OF 5-ARYL-1,3,4-OXADIAZOLE

Kut,

Krivovjaz

et al. 2023

Наук. вісник Ужг

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1,3,4-Oxadiazole and its functional derivatives have a wide spectrum of biological activity. There are well-known examples of the use of oxadiazoles in materials science as high-energy molecules. Therefore, the synthesis of new functional derivatives based on them is an urgent problem. This paper describes the synthesis of allylic thioethers of 5-nitrophenyl-1,3,4-oxadiazole by the alkylation reaction of the corresponding thiones with allyl bromide in an alcohol-alkaline medium. Such thioethers were studied in reactions with phenylselentrihalides, as a result of which oxadiazolo[2,3-d][1,3,4]thiaselenazinium halides were synthesized. We investigated the interaction of the tellurium-containing analogue p-methoxyphenyltellurium trichloride with allylic thioethers of 5-nitrophenyl-1,3,4-oxadiazole. It was established that the reaction between p-methoxyphenyl tellurium trichloride and the investigated alkenyl thioethers within 8 hours occurs with the formation of adducts of the substrate-electrophile composition 1:1, regardless of the ratio of reagents. Attempts to change the polarity of the solvent, increase the reaction time, and change the temperature regime did not change the direction of the reaction. Based on the obtained experimental spectral data and elemental analysis data, the structure of the obtained complexes is proposed. Keywords: p-methoxyphenyltellurium trichloride; 1,3,4-oxadiazole; allyl thioethers; organotellurium compounds; molecular complexes.

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COMPLEXES OF p-METHOXYPHENYLTELLURIUM TRICHLORIDE WITH ALLYL THIOETHERS OF 5-ARYL-1,3,4-OXADIAZOLE

Kut,

Krivovjaz

et al. 2023

Наук. вісник Ужг

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An eco‐friendly synthesis of 5‐aminotetrazoles using trichloroisocyanuric acid as desulfurization agent of thioureas

Moraes

Silva

Mattos

2023

Journal of Heterocyclic Chem

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A novel procedure for the preparation of various 5‐aminotetrazoles derivatives was achieved using trichloroisocyanuric acid as a desulfurizing agent of thioureas and trimethylsilyl azide in ethyl acetate at room temperature. This methodology provided substituted 5‐aminotetrazoles through a more sustainable reaction using an affordable, safe, stable, and easily handled N‐halo reagent, a safer azide source, and an environmentally friendly solvent.

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Triple Bond Species in the Synthesis of Oxa(thia)diazoles and Triazoles (A Review)

Gerasimova,

Egorov,

Egorova

et al. 2024

Russ J Gen Chem

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Tribromoisocyanuric acid as an alternative oxidant in the synthesis of 2-amino-1,3,4-oxadiazoles from 1-acylthiosemicarbazides

Cited by 5 publications

References 48 publications

COMPLEXES OF p-METHOXYPHENYLTELLURIUM TRICHLORIDE WITH ALLYL THIOETHERS OF 5-ARYL-1,3,4-OXADIAZOLE

COMPLEXES OF p-METHOXYPHENYLTELLURIUM TRICHLORIDE WITH ALLYL THIOETHERS OF 5-ARYL-1,3,4-OXADIAZOLE

An eco‐friendly synthesis of 5‐aminotetrazoles using trichloroisocyanuric acid as desulfurization agent of thioureas

Triple Bond Species in the Synthesis of Oxa(thia)diazoles and Triazoles (A Review)

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