Sodium dithionite in the regioselective reduction of the ortho-positioned nitro group in 1-R-2,4-dinitrobenzenes

Tsymliakov, Michael D.; Maksutova, Anita I.; Bezsonova, Elena N.; Zakharova, Daria V.; Grishin, Yu. K.; Тафеенко, В. А.; Sosonyuk, S. E.; Lozinskaya, N. A.

doi:10.1016/j.mencom.2023.01.038

Mendeleev Communications

2023

DOI: 10.1016/j.mencom.2023.01.038

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Sodium dithionite in the regioselective reduction of the ortho-positioned nitro group in 1-R-2,4-dinitrobenzenes

Michael D. Tsymliakov

Anita I. Maksutova

Elena N. Bezsonova

et al.

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2024

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Cited by 3 publications

References 31 publications

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Intermolecular Ipso Aromatic Nucleophilic Substitution of Electron‐Deficient Aryl Sulfonyl Chlorides

Mondal,

Roy,

Sikdar

et al. 2024

ChemistrySelect

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A mild and efficient approach is described for generating substitution products of electron‐deficient benzenesulfonyl chlorides via intermolecular ipso aromatic nucleophilic substitution reaction. Various amines and thiols effectively undergo a transition‐metal‐free coupling process, leading to diaryl or arylalkyl amines and thioethers with the formation of C─N and C─S bonds. The regioselective attack of N‐nucleophiles produces sulfonamides in the absence of a base. This reaction generates the Smiles rearrangement products. However, a series of mechanistic investigations point toward the intermolecular pathway in contrast to the intramolecular ipso substitution, known as Smiles rearrangement.

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Intermolecular Ipso Aromatic Nucleophilic Substitution of Electron‐Deficient Aryl Sulfonyl Chlorides

Mondal,

Roy,

Sikdar

et al. 2024

ChemistrySelect

View full text Add to dashboard Cite

show abstract

Fluorinated diaminobicyclooxacalixarene and diaminotetraoxacalixarenes: Synthesis and conformational behaviour

Han,

Kovtonyuk,

Gatilov

et al. 2024

Journal of Fluorine Chemistry

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Evaluation of the effects of some benzimidazole derivatives on germination parameters of wheat varieties

Külen,

Dincer

2024

J AGR SCI BELGRADE

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This study aims to investigate the effect of some benzimidazole derivatives on the germination parameters of bread and durum wheat varieties. These derivatives contain both unsubstituted and substituted benzimidazole structures to determine the effect of the substituents on germination. Three different durum wheat varieties (?e?it-1252, Eminbey, and K?z?ltan-91) and three different bread wheat varieties (Demir 2000, Bayraktar 2000, and Tosunbey) were used in the study. First, 1H-benzimidazole (1) and 5-nitro-1H-benzimidazole (2) compounds were used to synthesize dinitro compounds (5,6-dnitro-1H-benzimidazole (3), 5,6-dinitro-2-methyl-1H-benzimidazole (4)) in order to investigate the effects of wheat on germination characteristics. Subsequently, these compounds were each reduced to nitroamine compounds (2-methyl-5-nitro-1H-benzimidazole-6-amine (5), 5-nitro-1H-benzimidazole-6-amine (6)). Azo dyes (1-[(5-nitro-1H-benzimidazol-6-yl)diazenyl]naphthalene-2-ol (7), 1-[(2-methyl-5-nitro-1H-benzimidazol- 6-yl)diazenyl]naphthalene-2-ol (8)) and Schiff base compound (2-[(2-methyl-5-nitro-1H-benzimidazol-6-yl)imino]methyl}phenol (9)) were synthesized from nitroamine compounds. Wheat samples whose germination parameters were to be investigated were treated with benzimidazole derivatives synthesized at a concentration of 10-6M. Germination rates, coleoptile lengths, and root lengths of wheat varieties were measured on the 8th day of germination. The obtained results demonstrated that the efficiency of the benzimidazole compounds varied depending on the wheat varieties and germination parameters. 5-nitro-1H-benzimidazole-6-amine (6) had the greatest effect on germination rate while 1H-benzimidazole (1) had the greatest effect on root and coleoptile lengths in all varieties.

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Sodium dithionite in the regioselective reduction of the ortho-positioned nitro group in 1-R-2,4-dinitrobenzenes

Cited by 3 publications

References 31 publications

Intermolecular Ipso Aromatic Nucleophilic Substitution of Electron‐Deficient Aryl Sulfonyl Chlorides

Intermolecular Ipso Aromatic Nucleophilic Substitution of Electron‐Deficient Aryl Sulfonyl Chlorides

Fluorinated diaminobicyclooxacalixarene and diaminotetraoxacalixarenes: Synthesis and conformational behaviour

Evaluation of the effects of some benzimidazole derivatives on germination parameters of wheat varieties

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