Lewis acid-catalyzed chemo- and stereoselective addition of pyrroles to skipped diynones: en route to novel pyrrole-based ketocyanine dyes and alkyne-tethered enones

Dyes and Pigments, Год журнала: 2024, Номер 229, С. 112293 - 112293

Опубликована: Июнь 18, 2024

Язык: Английский

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Selective Synthesis of Functionalized 3(2H)‐Furanones via Tandem MichaelAddition/Rearrangement/Cyclization Reaction of Aliphatic Alkynones: A Combined Experimental and Theoretical Study

European Journal of Organic Chemistry, Год журнала: 2024, Номер 27(17)

Опубликована: Март 22, 2024

Abstract A novel catalyst‐ and solvent‐controlled dimerization of aliphatic alkynones through tandem Michael addition/rearrangement/cyclization sequence has been developed. The elaborated protocol provides a convenient chemo‐, regio‐ stereoselective access to rare 3(2 H )‐furanones decorated with 2‐ exo ‐methylene 4‐ethenyl functionalities. comprehensive density functional theory (DFT) study possible reaction mechanism including ab initio molecular dynamics (AIMD) simulations quantum atoms in molecules (QTAIM) analysis various substrate/catalyst/solvent complexes revealed the Janus‐like behavior employed sodium tert ‐butoxide/toluene system that is responsible both for chemoselectivity initial addition step inhibition final cyclization step.

Язык: Английский

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Indeno-Annulation of o-Formyl-Ynones, o-Bis-Ynones, and p-Bis-o-Formyl-Ynones with Dimethyl Acetone-1,3-Dicarboxylate: One Flask Cascade Synthesis of Functionally Endowed 9-Fluorenols and Indeno[1,2-b]fluorenols

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(16), С. 11637 - 11649

Опубликована: Авг. 9, 2023

A mild, scalable, one-pot access to multifunctional 9-fluorenols from o-formyl-ynones and o-bis-ynones on reaction with dimethylacetone-1,3-dicarboxyate through tandem Michael addition-Aldol condensation cascade has been conceptualized executed. The scope utility of this synthetic approach have further amplified for entry into functionally enhanced, higher order fluorenols like pentacyclic indeno[1,2-b]fluorene-6,12-diols indeno[1,2-b]fluorene-6,12-diones the implementation "double indeno-annulation" tactic p-bis-o-formyl ynones dimethylacetone-1,3-dicarboxylate. Besides several green attributes, current is also compatible emerging time energy economy features a swift gateway build complexity.

Язык: Английский

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Theoretical Investigation on Indeno-Annulation of O-Formyl-Ynone and P-Bis-O-Formyl-Ynone with Dimethylacetone-1,3-Dicarboxyate for Synthesis of 9‑Fluorenol and Indeno[1,2‑B]Fluorenol

Опубликована: Янв. 1, 2023

The mechanism is investigated for indeno-annulation of o-formyl-ynone, p-bis-o-formyl-ynone with DMAD under metal-free. cascade process consists Michael addition, aldol reaction condensation/aromatization. addition initiated by enol form via nucleophilic attack to ynone delivering accumulated diene the first new C−C bond. From ketone isomer, reaction/H transfer proceeds producing second bond and five-membered ring. enol-ketone tautomerism annulation are prior condensation affording third another six-membered fluorenol product given aromatization. positive solvation effect DMSO solution lies in reduction absolute activation energies reaction. exerts more favorable influence on simple CHO at ortho-position than case substituted this indeno-annulation. These results supported Multiwfn analysis FMO specific TSs MBO value vital bonding, breaking.

Язык: Английский

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Sequential [3+2] and [4+4] Annulation of Diynone and o‐Hydroxyaryl Azomethine Ylide: Construction of Dihydropyrrole Fused Eight‐Membered Ring Scaffold

Advanced Synthesis & Catalysis, Год журнала: 2023, Номер 365(23), С. 4175 - 4180

Опубликована: Ноя. 3, 2023

Abstract We developed a cascade reaction of diynone and o ‐hydroxy aromatic aldimine under mild conditions. This protocol is proposed to proceed through sequential [3+2]/[4+4] cycloaddition proton transfer processes, thus providing an efficient way for the synthesis variety dihydropyrrole fused eight‐membered ring scaffolds.

Язык: Английский

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Theoretical Investigation on Indeno-annulation of o-formyl-ynone and p-bis-o-formyl-ynone with Dimethylacetone-1,3-dicarboxyate for Synthesis of 9-fluorenol and Indeno[1,2-b]fluorenol

Acta Scientific Pharmaceutical Sciences, Год журнала: 2024, Номер unknown, С. 03 - 13

Опубликована: Фев. 1, 2024

The mechanism is investigated for indeno-annulation of o-formyl-ynone, p-bis-o-formyl-ynone with DMAD under metal-free.The cascade process consists Michael addition, aldol reaction condensation/aromatization.Michael addition initiated by enol form via nucleophilic attack to ynone delivering accumulated diene the first new C-C bond.From ketone isomer, reaction/H transfer proceeds producing second bond and five-membered ring.The enol-ketone tautomerism annulation are prior condensation affording third another six-membered fluorenol product given aromatization.The positive solvation effect DMSO solution lies in reduction absolute activation energies reaction.DMSO exerts more favorable influence on simple CHO at ortho-position than case substituted this indeno-annulation.These results supported Multiwfn analysis FMO specific TSs MBO value vital bonding, breaking.As a prime objective chemical industry, development synthetic methodologies not only essential sustainable production chemicals but also related efficiency, step, cost environmental impact minimize waste ecological footprint [1-3].In pursuit goal, catalysis discipline offering efficient versatile strategies sustainability especially formation multiple bonds presenting productive direction.It enables expansion enrichment domino or tandem processes executed one flask one-pot fashion thus minimizing number purification separation steps [4-6].The construction various polycyclic scaffolds such tactics provides privileged category expeditious delivery functional complex potential drug conjugates involving wide range pharmacological activities [7-9].In field, ynones regarded as promising platforms many reactive sites build [10].The reactions variety multifunctional partner often unraveled space.A was achieved Ru-catalyzed oxidative alkynylation oxetanols, azetidinols bicyclopentanols ynones, which subsequently converted azetidine-, oxetaneand bicyclopentane-bearing isoxazoles, pyrazoles pyrimidines [11].Conjugated alkynones occupied firm position among building blocks.The base-catalyzed substrate-controlled dimerizations aliphatic were focused density theory (DFT) study understand origin selectivity assembly [12].The cyclization diazo compounds promoted DBU has been developed synthesis fused eight-membered oxocino[2,3-c] single step highly regio-and diastereoselective manner [13].

Язык: Английский

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Brønsted Acid Promoted Reactions of γ-Hydroxy Acetylene Ketones. DFT Study of Cationic Intermediates and Concurrent Formation of 3-Furanones and/or Conjugated Enynones

Russian Journal of General Chemistry, Год журнала: 2024, Номер 94(S1), С. S138 - S147

Опубликована: Янв. 1, 2024

Язык: Английский

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Synthesis of 5-Amino-3(2H)-furanones via S-Methylation/Intramolecular Cyclization of γ-Sulfanylamides

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(10), С. 6770 - 6782

Опубликована: Май 1, 2024

The

Язык: Английский

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One flask cascade approach to complex pyrano[2,3-c]pyrazole-pyrazolone hybrid heterocyclic system and its initiatory neurobiological profiling

Chemical Communications, Год журнала: 2024, Номер 60(64), С. 8443 - 8446

Опубликована: Янв. 1, 2024

A one-pot multicomponent approach towards a hybrid heterocyclic pyrano[2,3-

Язык: Английский

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Synthesis of Spirocyclic‐1,3‐indandione Containing‐Cyclopentenones and ‐Benzotropones

Chemistry - An Asian Journal, Год журнала: 2024, Номер 19(20)

Опубликована: Июль 31, 2024

Synthesis of functionalized 1,3-indandiones containing-cyclopentenones and -benzotropones has been achieved by the reaction 1,5-diphenylpenta-1,4-diyn-3-ones with 1,3-indandiones, bindone respectively. The developed method involves Michael-anti-Michael addition cascade reactions under transition-metal-free conditions. This is first report to synthesise diverse benzotropone fused transition metal-free conditions from bindone.

Язык: Английский

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