Efficient synthesis of 3-selanyl- and 3-sulfanylindoles employing trichloroisocyanuric acid and dichalcogenides

Silveira, Cláudio C.; Mendes, Samuel R.; Wolf, Lucas; Martins, Guilherme M.; Mühlen, Lisandro von

doi:10.1016/j.tet.2012.09.022

Cited by 58 publications

(24 citation statements)

References 51 publications

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“…: 102–104 °C, lit. : 108.1–109.4 °C; Yield: 0.152 g (87 %); 1 H NMR (CDCl 3 , 400 MHz): δ =8.47 (s, 1 H), 7.76 (d, J= 1.9 Hz, 1 H), 7.42 (d, J= 2.6 Hz, 1 H), 7.31 (dd, J= 8.6, 1.9 Hz, 1 H), 7.26–7.11 ppm (m, 6 H); 13 C NMR (CDCl 3 , 100 MHz): δ =135.0, 133.3, 132.4, 131.8, 129.0, 128.6, 125.9, 125.8, 122.9, 114.3, 112.9, 97.7 ppm; MS m / z (rel. int.…”

Section: Methodsmentioning

confidence: 99%

“…In contrast to 3‐sulfenylindoles and 3‐sulfenylimidazo[1,2‐ a ]pyridines, for which the synthesis and pharmacological studies are well described, the number of papers on the synthesis and pharmacology of the selenium analogs is limited …”

Section: Introductionmentioning

confidence: 99%

“…Among the few methods for the synthesis of 3‐selanylindoles, the electrophilic aromatic substitution reaction (S E Ar) appears as the most applied strategy to incorporate the organoselenium group in such electron‐rich heterocycles. Diorganyl diselenides in combination with I 2 /FeCl 3 , (NH 4 ) 2 S 2 O 8 (only one example), I 2 /DMSO, I 2 /EtOH (only two examples), I 2 /FeF 3 (only two examples), trichloroisocyanuric acid, or copper salts have been used to prepare 3‐selanylindoles. Alternatively, previously prepared electrophilic selenium species, such as organylselenium halides, have been employed instead of diorganyl diselenides .…”

Section: Introductionmentioning

confidence: 99%

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Ultrasound‐Assisted Synthesis and Antioxidant Activity of 3‐Selanyl‐1 H‐indole and 3‐Selanylimidazo[1,2‐a]pyridine Derivatives

et al. 2017

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As imple and rapid methodf or the selective synthesis of 3-(organylselanyl)-1 H-indoles and3 -(organylselanyl)imidazo[1,2-a]pyridines catalyzed by CuI/SeO 2 under ultrasound irradiation was developed. This protocol employs adiverse range of 1 H-indoles or imidazo[1,2-a]pyridines and diorganyl diselenides to afford the corresponding products selectively in good to excellent yields. Moreover,t he antioxidant activity of these compounds was evaluated by using aw ider ange of in vitro assays,s uch as 2-azinobis-3-ethylbenzothiazoline-6-sulfonic acid (ABTS), 2,2-diphenyl-1picrylhydrazyl (DPPH) radical, ferric ion reducing antioxidant power (FRAP), and inhibition of reactive speciesf ormation in mice cortex. The bioassays revealed thatb oth classes of the newly synthesized organoselenium compounds present antioxidanta ctivity,w ith emphasis on the 3-(organylselanyl)-1 Hindoles.T his pharmacological activity opens aw ide range of biological applications where the reduction of oxidative stress is essential.[a] B. Results and DiscussionAc omparatives tudy on the use of microwaves, US, and conventional heating in the copper-catalyzed selenylation of indoles in DMSO was recently reported by us. [18b] In this reaction, Figure 1. 3-Arylselanylindoles A and B and 3-thioimidazo[1,2-a]pyridines C and D with similar effects to Combretastatin A-4a nd Enviroxime.Scheme1.Generalscheme of the present work.

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Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Ultrasound‐Assisted Synthesis and Antioxidant Activity of 3‐Selanyl‐1 H‐indole and 3‐Selanylimidazo[1,2‐a]pyridine Derivatives

et al. 2017

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“…[44] Organochalcogen compounds can be oxidized to radical anions or transformed into cations in a reversible process, according to the reaction conditions. The main reactions include the addition of an organochalcogen to double or triple bonds, [45,46] electrophilic addition to electron-rich arenes, [47,48] catalysis with selenium reagents, [49] transition metal catalysis, [50,51] cyclisation, [52,53] and application as ligands in catalysis. [54,55]…”

Section: Introductionmentioning

confidence: 99%

Recent Advances in Electrochemical Chalcogen (S/Se)‐Functionalization of Organic Molecules

et al. 2019

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Achieving advances in the development of clean and efficient synthetic routes has become an important aim in research. In recent years, the search for new sustainable methodologies, notably environmentally benign synthetic procedures, has gained the attention of the scientific community. Electrosynthesis is a tool that has been extensively studied due to its potential application in chemical transformations and it adheres to the principles of green chemistry. Organochalogen compounds form an important class of molecules, since many of them have properties that can be applied in medicine and materials science. Thus, herein we provide a comprehensive and updated overview covering recent advances in the electrochemical C(sp2)−H bond chalcogenation of activated arenes and heterocycles as well as electrochemical chalcogenation through oxidative cross‐coupling reactions and chalcogen‐functionalization of alkenes/alkynes. The scope, limitations, and mechanisms are described and discussed, detailing the fundamental aspects and benefits of electrochemistry for the chalcogenation of organic compounds. The content of this Minireview demonstrates that it is possible to provide new synthetic routes and to improve the existing methodologies, to obtain processes more in line with current environmental protection aims. The reader will also find a discussion on the fundamental aspects and benefits of applying electrosynthesis to the assembly and operation of an electrolytic cell.

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“…On the other hand, using metal‐like behavior of molecular iodine as catalyst, under microwave (MW) irradiation this protocol can promote the direct reaction of indoles with diselenides . In addition, catalyst free selenation of indoles with diselenides and oxidant trichloroisocyanuric acid (TCCA) or ammonium persulfate was another method . More recently, Braga's group demonstrated a green procedure for affording 3‐selanylindoles, they fount that only adding a catalytic amount of K 2 CO 3 in ethanol, the reaction of indoles with diselenides proceeded efficiently and gave the products in good yields by a radical pathway .…”

Section: Introductionmentioning

confidence: 99%

Selective synthesis of 3‐Selanylindoles from Indoles and Diselenides using IK/mCPBA system

Wang

Yan

2017

Applied Organom Chemis

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In the presence of a catalytic amount of KI combined with oxidant mCPBA, a convenient catalytic procedure is developed for the preparation of 3-selanylindoles from indoles and diselenides. In this protocol, KI is first oxidized by mCPBA into hypoiodous acid, which reacts with diselenide to cleave Se-Se bond. The in situ generated active electrophilic selenium species then reacts with indole, affording 3-selanylindole via an electrophilic substitution mechanism. This catalytic selenation of indoles has mild reaction conditions and is a simple procedure, which extends the synthetic application of KI in organic synthesis.

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Efficient synthesis of 3-selanyl- and 3-sulfanylindoles employing trichloroisocyanuric acid and dichalcogenides

Cited by 58 publications

References 51 publications

Ultrasound‐Assisted Synthesis and Antioxidant Activity of 3‐Selanyl‐1 H‐indole and 3‐Selanylimidazo[1,2‐a]pyridine Derivatives

Ultrasound‐Assisted Synthesis and Antioxidant Activity of 3‐Selanyl‐1 H‐indole and 3‐Selanylimidazo[1,2‐a]pyridine Derivatives

Recent Advances in Electrochemical Chalcogen (S/Se)‐Functionalization of Organic Molecules

Selective synthesis of 3‐Selanylindoles from Indoles and Diselenides using IK/mCPBA system

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