Calcium-mediated one-pot preparation of isoxazoles with deuterium incorporation

Ledovskaya, Maria S.; Rodygin, Konstantin S.; Ananikov, Valentine P.

doi:10.1039/c7qo00705a

Cited by 52 publications

(37 citation statements)

References 49 publications

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“…In many cases (if the reaction is tolerant to water and Ca(OH) 2 ) a simple single‐vessel setup can be utilized (Figure A). Calcium hydroxide released after the reaction of CaC 2 with water may even serve as an additional in situ formed base . Phase separation in a single reaction vessel may be achieved by using a carefully selected mixture of solvents (Figure B) .…”

Section: Sustainable Access Usage and Recycling Of Calcium Carbidementioning

confidence: 99%

“…For this reason, the synthesis of new deuterated substances is increasingly in demand in medicinal and pharmaceutical fields. A recently developed synthetic approach to prepare isoxazoles, with deuterium incorporation on request, is based on 1,3‐dipolar cycloaddition of nitrile oxide, which is generated from chloroaldoximes in the presence of a base, with the in situ generated acetylene or deuteroacetylene (Scheme ) . Another type of cycloaddition reaction with calcium carbide promoted by nitrous oxide is the Pauson–Khand reaction.…”

Section: Sustainable Access Usage and Recycling Of Calcium Carbidementioning

confidence: 99%

“…Ar ecently developed synthetic approach to prepare isoxazoles, with deuterium incorporation on request, is based on 1,3-dipolar cycloaddition of nitrile oxide, which is generated from chloroaldoximes in the presence of a base, with the in situ generateda cetylene or deuteroacetylene (Scheme 7). [24] Another type of cycloaddition reaction with calcium carbide promoted by nitrous oxide is the Pauson-Khand reaction. The cobalt-catalyzed intermolecularp rocess leads to ac yclopentenone in agood yield.…”

Section: Chemical Synthesis and Practical Applications Of Calcium Carmentioning

confidence: 99%

“…Calcium hydroxide released after the reactiono fC aC 2 with water maye ven serve as an additional in situ formed base. [24] Phase separation in as ingle reaction vessel may be achieved by using ac arefully selected mixture of solvents (Figure2B). [25] Am ore general setup includes standard two-vessel reactors (H-tube, etc.)…”

Section: Introductionmentioning

confidence: 99%

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Calcium‐Based Sustainable Chemical Technologies for Total Carbon Recycling

2019

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Calcium carbide, a stable solid compound composed of two atoms of carbon and one of calcium, has proven its effectiveness in chemical synthesis, due to the safety and convenience of handling the C≡C acetylenic units. The areas of CaC2 application are very diverse, and the development of calcium‐mediated approaches resolves several important challenges. This Review aims to discuss the laboratory chemistry of calcium carbide, and to go beyond its frontiers to organic synthesis, life sciences, materials and construction, carbon dioxide capturing, alloy manufacturing, and agriculture. The recyclability of calcium carbide and the availability of large‐scale industrial production facilities, as well as the future possibility of fossil‐resource‐independent manufacturing, position this compound as a key chemical platform for sustainable development. Easy regeneration and reuse of the carbide highlight calcium‐based sustainable chemical technologies as promising instruments for total carbon recycling.

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Section: Sustainable Access Usage and Recycling Of Calcium Carbidementioning

confidence: 99%

Section: Sustainable Access Usage and Recycling Of Calcium Carbidementioning

confidence: 99%

Section: Chemical Synthesis and Practical Applications Of Calcium Carmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Calcium‐Based Sustainable Chemical Technologies for Total Carbon Recycling

2019

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“…Cycloaddition reactions with acetylene ( Scheme 1 , path h ) provide a shortcut to isoxazoles, pyrazoles, and triazoles [ 41 , 42 , 43 , 44 ]. This segment of acetylene chemistry is especially promising for obtaining novel heterocyclic molecules.…”

Section: Introductionmentioning

confidence: 99%

Acetylene in Organic Synthesis: Recent Progress and New Uses

et al. 2018

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Recent progress in the leading synthetic applications of acetylene is discussed from the prospect of rapid development and novel opportunities. A diversity of reactions involving the acetylene molecule to carry out vinylation processes, cross-coupling reactions, synthesis of substituted alkynes, preparation of heterocycles and the construction of a number of functionalized molecules with different levels of molecular complexity were recently studied. Of particular importance is the utilization of acetylene in the synthesis of pharmaceutical substances and drugs. The increasing interest in acetylene and its involvement in organic transformations highlights a fascinating renaissance of this simplest alkyne molecule.

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Palladium‐Catalyzed One‐Pot Four‐Component Synthesis of β‐Cyano‐α,β‐unsaturated Ketones Using Calcium Carbide as an Acetylene Source and Potassium Hexacyanoferrate(II) as an Eco‐Friendly Cyanide Source

Hao

2019

Adv Synth Catal

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Palladium-catalyzed one-pot four-component synthesis of β-cyano-α,β-unsaturated ketones by the reactions of aryl halides, calcium carbide, potassium hexacyanoferrate(II) and aroyl chlorides is described. The salient features of this protocol are the direct use of easy-to-handle acetylene source and eco-friendly cyanide source, wide scope of substrates with good functional group tolerance, and simple work-up procedure.

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Calcium-mediated one-pot preparation of isoxazoles with deuterium incorporation

Abstract: In this work, a novel synthetic methodology for the one-pot preparation of isoxazoles directly from the reaction of calcium carbide with aldoximes is reported.

Cited by 52 publications

References 49 publications

Calcium‐Based Sustainable Chemical Technologies for Total Carbon Recycling

Calcium‐Based Sustainable Chemical Technologies for Total Carbon Recycling

Acetylene in Organic Synthesis: Recent Progress and New Uses

Palladium‐Catalyzed One‐Pot Four‐Component Synthesis of β‐Cyano‐α,β‐unsaturated Ketones Using Calcium Carbide as an Acetylene Source and Potassium Hexacyanoferrate(II) as an Eco‐Friendly Cyanide Source

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