Neue N,s-Substituierte Dienverbindungen Aus Reaktionen Von Mono(arylthio)substituierten Polyhalo-2-Nitrodienen Mit Aminen

Ibis, Cemil; Yilmaz, Nihal

doi:10.1080/10426500008043653

Cited by 20 publications

(2 citation statements)

References 14 publications

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“…Reactions of polyhalo-dienes and -butenes with thiols or amines have been previously reported by Ibis and co-workers and Roedig and coworkers (12)(13)(14)(15)(16)(17)(18)(19)(20)(21)(22)(23)(24)(25)(26). Yoshimatsu et al reported the preparation of 2-sulfonyl-1-buten-3-ynes and their reactions with nucleophiles (9).…”

Section: Introductionmentioning

confidence: 86%

Synthesis of (Thio)substituted -1,3-Butadienes and -Butenynes

Kaçmaz

2019

Journal of the Turkish Chemical Society Section A: Chemistry

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In this study, 2H-1,1,3,4,4-pentachloro-1,3-butadiene (1) was reacted with different thiols (2methyl-2-propanethiol 2a, benzyl mercaptan 2b, 4-tert-butylbenzenethiol 2c, 4-nitrothiophenol 2d) in ethanol in the presence of NaOH to afford mono-thio-substituted-1,3-butadienes and mono-and tris-thiosubstituted-1-buten-3-ynes. Among them, (4-tert-butylphenyl)(1,3,4,4-tetrachlorobuta-1,3dienyl)sulfane (4c) exhibited two isomers of mono products. Moreover, the reaction of compound (1) with 2-hydroxythiophenol (2e) in dimethylformamide in the presence of triethylamine took place the formation of OH-protected butadiene structure 2-((Z)-1,3,4,4-tetrachlorobuta-1,3-dienylthio)phenol (4e) and ringclosed butadiene structure (E)-2-(2,3,3-trichloroallylidene)benzo[d][1,3]oxathiole (6), together and with two isomers of each. Their structures identified on the basis of GC-MS(+EI) analysis with different retention times (RT). Characterization of the synthesized compounds was done using several methods, mass spectrometry (GC-MS(+EI)), 1 H-, 13 C-, APT-NMR, FTIR and elemental analysis.

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Section: Introductionmentioning

confidence: 86%

Synthesis of (Thio)substituted -1,3-Butadienes and -Butenynes

Kaçmaz

2019

Journal of the Turkish Chemical Society Section A: Chemistry

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“…[29][30][31] Various S-and N,S-substituted polyhalo-2-nitrobuta-1,3-diene compounds were synthesized in our previous studies. [30,[32][33][34][35] In this work, enzyme, inhibition and antioxidant activity study of these com-pounds were done by synthesizing new derivatives of N,S-substituted polyhalo-2-nitrobuta-1,3-diene.…”

Section: Synthesismentioning

confidence: 99%

Synthesis and antioxidant, antixanthine oxidase, and antielastase activities of novel N,S‐substituted polyhalogenated nitrobutadiene derivatives

Onul

Ertik

Mermer

et al. 2017

J Biochem & Molecular Tox

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In this study, three substituted polyhalogenated nitrobutadiene derivatives were synthesized. Compound 1-[(2,3-dibromopropyl)sulfanyl]-1,3,4,4-tetrachloro-2-nitrobuta-1,3-diene (4) was synthesized before by our group. Compounds 8-{[1-[(2,3-dibromopropyl)sulfany]-3,4,4-trichloro-2-nitrobuta-1,3-butadien-1-yl}-1,4-dioxa-8-azaspiro[4.5]decane (5) and 1-[(2,3-dibromopropyl)sulfanyl]-3,4,4-trichloro-N-(4-methylpiperazin-1-yl)-2-nitrobuta-1,3-diene-1-amine (6) were synthesized in this work as original compounds. Xanthine oxidase, elastase inhibition abilities, and antioxidant activities were investigated in this work for compounds 4, 5, and 6. In this study, compounds 4, 5, and 6 exhibited antixanthine oxidase, antielastase, and antioxidant activities. Among the compounds screened, compound 4 exhibited xanthine oxidase and elastase inhibitor effect similar to the standard compound. Among the three tested compounds, compound 6 showed potent DPPH radical scavenging and reducing power activities. Therefore, these three compounds (4, 5, and 6) may be useful as an antixanthine oxidase, antielastase, and antioxidant agent in pharmaceutical and cosmetic industry.

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