A new class of sulfur‐linked bis‐1,2,3‐selenadiazoles, 1,2,3‐thiadiazoles, and 2<i>H</i>‐diazaphospholes

Padmavathi, V.; Mahesh, Konda; Subbaiah, D. R. C. Venkata; Padmaja, A.

doi:10.1002/hc.20425

Cited by 7 publications

(4 citation statements)

References 11 publications

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“…More recently, ethoxycarbonyl hydrazones and tosylhydrazones were also used for the reaction with SeO 2 in acetic acid. A number of works on the synthesis and use of 1,2,3-selenadiazoles has been discussed in reviews [9,90,91,92] and in more recently published original papers [93,94,95,96,97,98,99,100]. Synthesis of novel benzopyrano-1,2,3-selenadiazole and spiro[benzopyrano]-1,3,4-thiadiazoline derivatives as possible antitumor agents is an example [96].…”

Section: Selenium(iv) Oxide and Selenic(iv) Acid As Oxidizing Agenmentioning

confidence: 99%

Developments in Synthetic Application of Selenium(IV) Oxide and Organoselenium Compounds as Oxygen Donors and Oxygen-Transfer Agents

2015

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A variety of selenium compounds were proven to be useful reagents and catalysts for organic synthesis over the past several decades. The most interesting aspect, which emerged in recent years, concerns application of hydroperoxide/selenium(IV) oxide and hydroperoxide/organoselenium catalyst systems, as "green reagents" for the oxidation of different organic functional groups. The topic of oxidations catalyzed by organoselenium derivatives has rapidly expanded in the last fifteen years This paper is devoted to the synthetic applications of the oxidation reactions mediated by selenium compounds such as selenium(IV) oxide, areneseleninic acids, their anhydrides, selenides, diselenides, benzisoselenazol-3(2H)-ones and other less often used other organoselenium compounds. All these compounds have been successfully applied for various oxidations useful in practical organic syntheses such as epoxidation, 1,2-dihydroxylation, and α-oxyfunctionalization of alkenes, as well as for ring contraction of cycloalkanones, conversion of halomethyl, hydroxymethyl or active methylene groups into formyl groups, oxidation of carbonyl compounds into carboxylic acids and/or lactones, sulfides into sulfoxides, and secondary amines into nitrones and regeneration of parent carbonyl compounds from their azomethine derivatives. Other reactions such as dehydrogenation and aromatization, active carbon-carbon bond cleavage, oxidative amidation, bromolactonization and oxidation of bromide for subsequent reactions with alkenes are also successfully mediated by selenium (IV) oxide or organoselenium compounds. The oxidation mechanisms of ionic or free radical character depending on the substrate and oxidant are discussed. Coverage of the literature up to early OPEN ACCESSMolecules 2015, 20 10206 2015 is provided. Links have been made to reviews that summarize earlier literature and to the methods of preparation of organoselenium reagents and catalysts.

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Section: Selenium(iv) Oxide and Selenic(iv) Acid As Oxidizing Agenmentioning

confidence: 99%

Developments in Synthetic Application of Selenium(IV) Oxide and Organoselenium Compounds as Oxygen Donors and Oxygen-Transfer Agents

2015

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“…When diphenacyl sulfide 1a was allowed to react with phenylhydrazine in ethanol under reflux conditions for 30 min, it afforded bis (2-phenyl-2-(2-phenylhydrazono) ethyl)sulfane 5a. 15 Bishydrazone 5a subsequently reacted with con. HCl in ethanol yielding (82%) the bisindole 3a.…”

Section: Resultsmentioning

confidence: 99%

Solvent based selectivity in the synthesis of di(2-aryl-1H-3-indolyl) sulfides and 1-aryl-2-[(2-aryl-1H-3-indolyl)sulfanyl]-1-ethanones

et al. 2012

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“…The bis-1,2,3-selenadiazoles and thiadiazoles (13) were prepared and exhibited antimicrobial activity. 33 The 2,5-bis(4-pyridyl)-1,3,4-thiadiazole ligand formed a coordination polymer with cis-Pt(PMePh 2 ) 2 (NO 3 ) 2 . 34 The thiachalcazolylium cations (14 + , isoelectronic with 12 + ) were formed via the condensation of persilylated 2-aminobenzenethiol with ECl 4 (E = Se, Te).…”

Section: Chalcogen-nitrogen Systemsmentioning

confidence: 99%

“…54 Reaction of Woollins' reagent, [PhP(Se)(m-Se)] 2 , with alkyl diols and BuNH 2 yielded the ammonium salt of bis(diselenophosphonic) acid, 32. Reaction of this salt with MeI generated bis(phenyl-diselenophosphonic) acid Se,Se-dimethyl esters (33) whereas oxidation with I 2 /KI yields cyclic diselenides (34). 55,56 Reaction of Woollins' reagent with nitriles generates the heterocyclic selenazadiphospholaminediselenides [PhCH 2 CH 2 N(R)CQN(PhP(Se)SeP(Se)Ph] (35) and their hydrolysis products [PhCH 2 CH 2 N(R)-C(NH 2 )P(Se)(Se)Ph] (36) (R = H or Me).…”

Section: Chalcogen-phosphorus Systemsmentioning

confidence: 99%

Oxygen, sulfur, selenium, tellurium and polonium

Haynes

Melen

Rawson

2009

Annu. Rep. Prog. Chem., Sect. A: Inorg. Chem.

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A new class of sulfur‐linked bis‐1,2,3‐selenadiazoles, 1,2,3‐thiadiazoles, and 2H‐diazaphospholes

Abstract: Novel sulfur-linked bis-heterocycles, bis-1,2,3-selenadiazoles 4, 1,2,3-thiadiazoles 5, and 2H-diazaphospholes 7, were synthesized from bis(2oxo-2-phenylethanone)sulfide 2 by adopting a simple and well-versed methodology.

Cited by 7 publications

References 11 publications

Developments in Synthetic Application of Selenium(IV) Oxide and Organoselenium Compounds as Oxygen Donors and Oxygen-Transfer Agents

Developments in Synthetic Application of Selenium(IV) Oxide and Organoselenium Compounds as Oxygen Donors and Oxygen-Transfer Agents

Solvent based selectivity in the synthesis of di(2-aryl-1H-3-indolyl) sulfides and 1-aryl-2-[(2-aryl-1H-3-indolyl)sulfanyl]-1-ethanones

Oxygen, sulfur, selenium, tellurium and polonium

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