Trisubstituted push-pull nitro alkenes

Pavilek, Branislav; Milata, Viktor

doi:10.24820/ark.5550190.p011.495

Cited by 2 publications

(3 citation statements)

References 65 publications

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“…Nitroalkenoates are an emerging class of extremely powerful electrophiles because the nitro group is the most electron-withdrawing group known. [9,[65][66][67] However, in contrast to the rich chemistry of push-pull nitroalkenes bearing two acceptor substituents in geminal position [68] the reactivity of pull-pull nitroalkenes is much less explored.…”

Section: Conjugate Nucleophilic Addition To β-Nitroenoatesmentioning

confidence: 99%

Pull‐Pull Alkenes in the Aza‐Michael Reaction

Rulev

Tyumentsev

2022

Adv Synth Catal

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Aza‐Michael addition is known to be one of the most exploited reactions in organic chemistry. Taking into account the fact that each seventh reaction in pharmaceutical industry involves the formation of at least one C−N bond, it is not surprising that this reaction is especially valuable for the synthesis of bioactive compounds and drugs. Traditionally, only push‐pull alkenes are regarded as starting material for this reaction. The participation of pull‐pull alkenes as Michael acceptors is much less studied. The presence of two vicinal electron‐withdrawing groups makes them highly reactive in nucleophilic reactions especially with nitrogen‐centered nucleophiles. This feature allows them to be excellent building blocks in the synthesis of bioactive molecules and polyfunctional materials. The review considers the most important and sometimes unexpected results obtained over the last two decades on the conjugate addition of nitrogen nucleophiles to pull‐pull alkenes bearing various acceptor moieties (alkoxycarbonyl‐, carbonyl‐, formyl‐, cyano‐, trifluoromethyl‐ or nitro group) in various combinations.

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Section: Conjugate Nucleophilic Addition To β-Nitroenoatesmentioning

confidence: 99%

Pull‐Pull Alkenes in the Aza‐Michael Reaction

Rulev

Tyumentsev

2022

Adv Synth Catal

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“…Since, nitro-alkenes are synthetically useful precursors for the preparation of a wide variety of valuable organic molecules besides exhibiting outstanding biological properties. [139][140][141] Therefore, bearing in mind the importance of nitro-olefins, Hlekhlai et al exposed a useful protocol for the synthesis of βiodonitro alkenes from phenyl-acetylene derivatives 166 utilizing NaNO 2 /KI/oxone to assemble diverse styrene derivatives 167 a-d in practical yields as detailed in the Scheme 51. [64] Strikingly, these authors have exposed the utility of this versatile method for the systems containing both electron donating and electron withdrawing groups in the aromatic nucleus.…”

Section: Iodo-nitration Of Aromatic Alkynesmentioning

confidence: 99%

“…Since, nitro‐alkenes are synthetically useful precursors for the preparation of a wide variety of valuable organic molecules besides exhibiting outstanding biological properties [139–141] . Therefore, bearing in mind the importance of nitro‐olefins, Hlekhlai et al .…”

Section: Halogenationsmentioning

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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Trisubstituted push-pull nitro alkenes

Cited by 2 publications

References 65 publications

Pull‐Pull Alkenes in the Aza‐Michael Reaction

Pull‐Pull Alkenes in the Aza‐Michael Reaction

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

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