Oxone®-Promoted One-Pot Synthesis of 1-Aryl-4-(organylselanyl)-1H-pyrazoles

Jacob, Raquel G.; Hartwig, Daniela; Peglow, Thiago J.; Nascimento, José Edmilson R.; Bartz, Ricardo H.

doi:10.21577/0103-5053.20190094

Cited by 3 publications

(3 citation statements)

References 44 publications

(59 reference statements)

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“…It is worth to mention that species I and II, in the presence of MeOH and Oxone, can be converted to the methyl benzeneseleninate V and benzeneseleninic acid VI, respectively (Scheme 14). In the same year, Jacob and co-workers also reported the synthesis of 4-organoselanyl-1H-pyrazoles 22 through a multicomponent reaction between hydrazines 23, 1,3-diketones 24 and diorganyl diselenides 21, in the presence of Oxone (Scheme 15) [23]. In general, the protocol presented a good substrate tolerance, allowing the synthesis of twelve substituted 4-organylselanylpyrazoles 22 in moderate to excellent yields, after short reaction times.…”

Section: Nitrogen-containing Heterocyclesmentioning

confidence: 98%

Recent Advances in the Oxone-Mediated Synthesis of Heterocyclic Compounds

et al. 2021

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Oxone is a commercially available oxidant, composed of a mixture of three inorganic species, being the potassium peroxymonosulfate (KHSO5) the reactive one. Over the past few decades, this cheap and environmentally friendly oxidant has become a powerful tool in organic synthesis, being extensively employed to mediate the construction of a plethora of important compounds. This review summarizes the recent advances in the Oxone-mediated synthesis of N-, O- and chalcogen-containing heterocyclic compounds, through a wide diversity of reactions, starting from several kinds of substrate, highlighting the main synthetic differences, advantages, the scope and limitations.

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Section: Nitrogen-containing Heterocyclesmentioning

confidence: 98%

Recent Advances in the Oxone-Mediated Synthesis of Heterocyclic Compounds

et al. 2021

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“…[169][170][171][172][173][174] In this context, Bartz's group developed an efficient protocol for one-pot synthesis of 4-organylselanylpyrazoles 434 a-g by direct cyclocondensation and CÀ H bond selenylation starting from hydrazines,1,3diketones 432 and diorganyl diselenides 433in the presence of oxone/acetic acid under open flask (Scheme 138). [328] This method provided a large number of products under catalystfree condition in short reaction times in 44-98 % yields.…”

Section: Cleavage Of Se-se/te-te Bonds For the Formation Of Organocha...mentioning

confidence: 99%

Applications of Oxone® in Organic Synthesis: An Emerging Green Reagent of Modern Era

2022

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Presently, the major cornerstone of the research community is to develop green as well as sustainable protocols involving inexpensive catalysts and/or reagents without the usage of hazardous solvents under globally friendlier conditions in order to shelter both mankind and environment. Therefore, needless to say, there is always a supreme need to surrogate the older, costlier and unsafe strategies with the novel economically inexpensive and environmental benign ones. To this context, in recent past, oxone® (triple salt), a very cheap oxidizing agent having the chemical formula 2KHSO5 ⋅ KHSO4 ⋅ K2SO4 and enwrapped with the unique characteristics like easy handling, non‐toxic, safe, eco‐friendly, non‐polluting, stable, and nicely soluble in water, in addition to its utility for large‐scale synthesis etc. Bearing the importance of this versatile reagent in mind, we envisioned to update the recent advances made in this direction. Consequently, in this particular review article, the developments made in the arena of oxone chemistry covering from 2013 to 2020 have been revealed as no report appeared in the literature after a wonderful Chem. Rev. published by the group of Hussain in 2013. Herein, a comprehensive detail of a variety of oxidative transformations along with the complete plausible mechanistic steps have been exposed. For sure, present review would be a very helpful tool to the scientific community not only working in the area of organic synthesis but also to the researchers working in other branches of science and technologies as well.

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“…The electrophilic selenium species generated in situ reacted with 4a to give 2-phenyl-3-(phenylselanyl)selenopheno[2,3-b]pyridine 7 in 85% yield after 12 h (Scheme 5-B). 39 Scheme 5. Synthetic applications for compound 4a.…”

Section: Scheme 4 Proposed Mechanismmentioning

confidence: 99%

Synthesis of 2-organylselenopheno[2,3-b]pyridines and 1,6-diazaselenanthrenes via radical cascade reactions using tert-butyl nitrite

Perin¹,

Peglow²,

Bartz³

et al. 2019

Arkivoc

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We describe herein an alternative method to prepare 2-organylselenopheno [2,3-b]pyridines starting from bis(3-amino-2-pyridyl) diselenide and aryl-and alkylacetylenes in the presence of t BuONO in CH3NO2 as solvent. The reactions were conducted at 80 °C for 2 hours, and six selenopheno[2,3-b]pyridine derivatives were obtained in satisfactory yields, ranging from 10% to 41%. Using the same conditions, but in the absence of the alkyne counterpart, three new 1,6-diazaselenanthrenes were obtained with yields ranging from 41% to 47%. These compounds are unknown in the literature.

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Oxone®-Promoted One-Pot Synthesis of 1-Aryl-4-(organylselanyl)-1H-pyrazoles

Cited by 3 publications

References 44 publications

Recent Advances in the Oxone-Mediated Synthesis of Heterocyclic Compounds

Recent Advances in the Oxone-Mediated Synthesis of Heterocyclic Compounds

Applications of Oxone® in Organic Synthesis: An Emerging Green Reagent of Modern Era

Synthesis of 2-organylselenopheno[2,3-b]pyridines and 1,6-diazaselenanthrenes via radical cascade reactions using tert-butyl nitrite

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