The Synthesis of New S- and N,S-Substituted Halo Nitro Dienes by the Reactions of 1-Bromo-1,2,4,4-tetrachloro-3-nitrobuta-1,3-diene with Thiols and Cyclic Amines

Ibis, Cemil; Tuyun, Amaç Fatih; Aydınlı, Gökşin

doi:10.1080/10426500903453318

Cited by 9 publications

(1 citation statement)

References 19 publications

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“…Compounds 1a and 1b gave vinylic substitution reaction at room temperature and with the absence of solvent because of the reactivity of terminal carbon having nitrodichlorovinyl, and they yielded monosubstituted polyhalobutadiene compounds 3a [49] and 3b [50]. It has been reported that mono(thio)substitution nitrodienes are (E) isomers in previous studies [56][57][58]. As a consequence, it might be thought that derived new S-Substituted nitrodiene products were probably (E) isomers.…”

Section: Synthesis Of S-substituted Perhalonitrobuta-13-dienesmentioning

confidence: 99%

Synthesis and Biological Evaluation of S-Substituted Perhalo-2-nitrobuta-1,3-dienes as Novel Xanthine Oxidase, Tyrosinase, Elastase, and Neuraminidase Inhibitors

Onul

Ertik

Mermer

et al. 2018

Journal of Chemistry

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S-substituted perhalo-2-nitrobuta-1,3-dienes 3a, b were synthesized by the reaction of polyhalo-2-nitrobuta-1,3-dienes 1a, b with allyl mercaptan. 1-(2,3-Dibromopropanethio)-4-bromo-1,3,4-trichloro-2-nitrobuta-1,3-diene 4 was obtained from the addition of bromine to S-substituted polyhalo-2-nitrobuta-1,3-diene 3b in carbon tetrachloride. Sulfoxides 5a, b, and 6 were obtained from the reaction of thiosubstituted polyhalonitrobutadienes 3a, b, and 4 with m-CPBA in CHCl 3 . The structures of the new compounds were determined by spectroscopic data (FTIR, 1 H NMR, 13 C NMR, MS). These compounds exhibited antixanthine oxidase, antityrosinase, antielastase, and antineuraminidase activities.

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Section: Synthesis Of S-substituted Perhalonitrobuta-13-dienesmentioning

confidence: 99%

Synthesis and Biological Evaluation of S-Substituted Perhalo-2-nitrobuta-1,3-dienes as Novel Xanthine Oxidase, Tyrosinase, Elastase, and Neuraminidase Inhibitors

Onul

Ertik

Mermer

et al. 2018

Journal of Chemistry

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New Ketene Dithioacetals Generated from 2‐Nitroperchlorobutadiene and Investigation of Their Antibacterial, Antifungal, Anticonvulsant and Antidepressant Activities

Aydınlı

Bulut

Deniz

et al. 2022

Chemistry & Biodiversity

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The ketene dithioacetal 3 generated from 2‐nitroperchlorobutadiene 1 reacted with various heterocyclic amines and aliphatic, aromatic and heterocyclic thiols to produce functionalized new ketene‐N,S,S‐acetals and S,S,S‐acetals 4a–f, 5a–h as heterocyclic dithiolanes. They were separated/purified by chromatographic methods and their exact structure characterization were made clear by spectroscopic methods. These compounds synthesized could act as effective drugs for versatile activity. Evaluation of the antimicrobial effect of the obtained substances determined derivatives 4e and 5h, which have MIC=15.6 μg/mL for the test culture of Mycobacterium luteum bacteria closing to the control drug Vancomycin. The obtained compounds can be proposed as a promising synthetic objects for future molecular design to enhance the antimicrobial action. Ketene dithioacetals 3, 4a, 4b, 4e, 5g (50 mg/kg) exhibited antiseizure effect comparable with reference drug (valproic acid) on the model of pentylenetetrazole‐induced convulsions after single oral administration both at 3 h and 24 h. Furthermore, tested dithioacetals possessed prolonged antidepressant activity in forced swim test (FST) considerable decreasing the duration of immobility time compared to reference drug amitriptyline. This is the first study of the investigation of anticonvulsant and antidepressant activities of ketene dithioacetals.

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The Vinylic S_N Reactions of Nitrodienes with Heteroatom‐Substituted Nuchleophilies and Their Structural Studies

Deniz

Ibis

2014

Heteroatom Chemistry

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Herein, we report the reactions of 1,1,2,4,4‐pentachloro‐3‐nitro‐1,3‐butadiene 1a and (1Z)‐1‐bromo‐1,2,4,4‐tetrachloro‐3‐nitro‐1,3‐butadiene 1b with nitrogen‐ and sulfur‐containing nucleophiles to obtain highly functionalized S‐, S,S‐, S,S,S‐, S,O‐ and N,S‐substituted‐polyhalodiene‐3‐nitro‐1,3‐butadiene derivatives. Most of these reactions turned out to be highly selective with good to very good yields. All new compounds have been characterized by nuclear magnetic resonance spectroscopy, mass spectrometry, and Fourier transform infrared spectroscopy spectroscopic data. The molecular structures of the 3a and 21a due to its exceptional substitution pattern were evidenced by the X‐ray single‐crystal diffraction method.

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The Synthesis of New S- and N,S-Substituted Halo Nitro Dienes by the Reactions of 1-Bromo-1,2,4,4-tetrachloro-3-nitrobuta-1,3-diene with Thiols and Cyclic Amines

Cited by 9 publications

References 19 publications

Synthesis and Biological Evaluation of S-Substituted Perhalo-2-nitrobuta-1,3-dienes as Novel Xanthine Oxidase, Tyrosinase, Elastase, and Neuraminidase Inhibitors

Synthesis and Biological Evaluation of S-Substituted Perhalo-2-nitrobuta-1,3-dienes as Novel Xanthine Oxidase, Tyrosinase, Elastase, and Neuraminidase Inhibitors

New Ketene Dithioacetals Generated from 2‐Nitroperchlorobutadiene and Investigation of Their Antibacterial, Antifungal, Anticonvulsant and Antidepressant Activities

The Vinylic S_N Reactions of Nitrodienes with Heteroatom‐Substituted Nuchleophilies and Their Structural Studies

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The Synthesis of New S- and N,S-Substituted Halo Nitro Dienes by the Reactions of 1-Bromo-1,2,4,4-tetrachloro-3-nitrobuta-1,3-diene with Thiols and Cyclic Amines

Cited by 9 publications

References 19 publications

Synthesis and Biological Evaluation of S-Substituted Perhalo-2-nitrobuta-1,3-dienes as Novel Xanthine Oxidase, Tyrosinase, Elastase, and Neuraminidase Inhibitors

Synthesis and Biological Evaluation of S-Substituted Perhalo-2-nitrobuta-1,3-dienes as Novel Xanthine Oxidase, Tyrosinase, Elastase, and Neuraminidase Inhibitors

New Ketene Dithioacetals Generated from 2‐Nitroperchlorobutadiene and Investigation of Their Antibacterial, Antifungal, Anticonvulsant and Antidepressant Activities

The Vinylic SN Reactions of Nitrodienes with Heteroatom‐Substituted Nuchleophilies and Their Structural Studies

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The Vinylic S_N Reactions of Nitrodienes with Heteroatom‐Substituted Nuchleophilies and Their Structural Studies