Construction of 3-Methyl-2-Substituted Benzo[b]furans and 3-Methyl-2-Substituted Benzo[b]thiophenes Using Solid Calcium Carbide as a Substitute for Gaseous Acetylene

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(10), P. 7182 - 7186

Published: May 2, 2024

A concise method for the facile construction of 3-methyl-2-substituted benzo[b]furans and benzo[b]thiophenes using low-cost, abundant, easy-to-use solid calcium carbide instead flammable explosive gaseous acetylene as an original alkyne source, o-bromophenyl ethers or thioethers substrates through intramolecular carbanion-yne cyclization in a 5-exo-dig manner, subsequent double-bond isomerization is described. The simultaneous formation two C–C bonds realized one-step route. wide substrate scope, high yield, simple workup manipulations are also merits this method. synthetic strategy can be suitable gram scale.

Language: Английский

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Construction of Pyrazolo[1,5-a]pyrimidines and Pyrimido[1,2-b]indazoles with Calcium Carbide as an Alkyne Source

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(28), P. 5822 - 5826

Published: Jan. 1, 2024

One-step construction of both 5-arylpyrazolo[1,5- a ]pyrimidines and 2-arylpyrimido[1,2- b ]indazoles using inexpensive, abundant easy-to-handle calcium carbide as solid alkyne source is depicted.

Language: Английский

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Highly Stereoselective Synthesis of 2-Acyl-3-sulfonamidobut-2-enoates Using Solid Calcium Carbide as a Substitute for Gaseous Acetylene

Organic Letters, Journal Year: 2024, Volume and Issue: 26(29), P. 6269 - 6273

Published: July 17, 2024

Multifunctional group compounds, 2-acyl-3-sulfonamidobut-2-enoates, are efficiently constructed using solid calcium carbide as an alkyne source through the simultaneous formation of two bonds in one step. The salient features this protocol use inexpensive, abundant, and easy-to-use a substitute for flammable explosive gaseous acetylene, low-cost catalyst, mild conditions, wide substrate scope, high stereoselectivity, satisfactory yield, simple manipulation. This method can also be extended to gram scale.

Language: Английский

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One-step construction of indolo[2,1- a ]isoquinolines using solid calcium carbide as an alternative to gaseous acetylene

Synthetic Communications, Journal Year: 2024, Volume and Issue: 54(14), P. 1209 - 1219

Published: July 17, 2024

Language: Английский

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Vinylation of Alcohols, Thiols, and Nitrogen Compounds Using a Stoichiometric Amount of In Situ Generated Acetylene

Organics, Journal Year: 2025, Volume and Issue: 6(1), P. 5 - 5

Published: Feb. 8, 2025

In this work, we developed a highly efficient and versatile environmentally benign methodology for the vinylation of broad scope substances, including alcohols, thiols, nitrogen compounds. The key advantage proposed method is use calcium carbide as robust acetylene source in stoichiometric ratio to substrates. Lacking requirement excess, protocol safe, economic, limits waste production. procedure allows large variety O-,S-,N-vinyl compounds be synthesized up quantitative yields. Our scalable, allowing us obtain vinyl derivatives Gram-scale quantities. We also demonstrated significant synthetic value our approach by performing label-economic synthesis 13C2-labeled using carbide-13C2. well-optimized process, conversion Ca13C2 reached 89%.

Language: Английский

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Synthesis of Spirocyclic Phthalans via Ru-Catalyzed [2 + 2 + 2] Cycloaddition of 1,6-Diynes with Ex-Situ Generated Acetylene

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: April 15, 2025

Spirocyclic motifs are attracting increasing attention owing to their three-dimensional geometries that endow bioactive molecules with superior physical and biological properties. We developed an efficient method for constructing spirocyclic phthalans via the Ru-catalyzed [2 + 2 2] cycloaddition of cycloalkanone-derived 1,6-diynes acetylene gas ex-situ-generated from calcium carbide H2O.

Language: Английский

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The Use of Calcium Carbide for Cyclopentenone Ring Construction

Russian Journal of General Chemistry, Journal Year: 2024, Volume and Issue: 94(1), P. 45 - 48

Published: Jan. 1, 2024

Language: Английский

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Three-component one-pot construction of 2-aryl-3-benzylbenzo[4,5]imidazo[1,2- a ]pyrimidines using solid calcium carbide as an alkyne source

Synthetic Communications, Journal Year: 2025, Volume and Issue: unknown, P. 1 - 11

Published: Feb. 16, 2025

Language: Английский

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Recent progress in the catalytic transformation of acetylene

Chemical Society Reviews, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

Acetylene, a traditional industrial raw material, has garnered increasing attention in modern organic synthesis over the past two decades.

Language: Английский

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One‐Pot Three‐Component Construction of (Z)‐3‐Benzylidene‐2‐(quinolin‐8‐yl)isoindolin‐1‐ones Through C(sp²)−H Bond Activation Using Calcium Carbide as a Solid Alkyne Source

ChemistrySelect, Journal Year: 2024, Volume and Issue: 9(33)

Published: Sept. 4, 2024

Abstract A simple method for the synthesis of (Z)‐3‐benzylidene‐2‐(quinolin‐8‐yl)isoindolin‐1‐ones through C(sp 2 )−H bond activation, Sonogashira cross‐coupling and annulation tandem reactions using calcium carbide as a solid alkyne source, benzamides starting materials is described. The inexpensive easy‐to‐handle first employed coupling partner in non‐activated activation. one‐pot three‐component proceed efficiently with broad range substrates good tolerance diversity functional groups. reaction routes can also be scaled up to gram scale.

Language: Английский

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