One-Pot Three-Component Synthesis of Indolyl-4H-chromene-3-sulfonyl Fluoride: A Class of Important Pharmacophore

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(5), С. 3618 - 3628

Опубликована: Фев. 15, 2024

A one-pot, sequential three-component reaction between salicylaldehyde, indole, and 2-bromoprop-2-ene-1-sulfonyl fluoride (BPESF) has been demonstrated for the synthesis of sulfonyl substituted 4H-chromene derivatives in moderate to excellent yields (45%–94%). This one-pot method features easily available starting materials, wide substrate scope, mild conditions, great efficiency.

Язык: Английский

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Mn(OAc)₃-Mediated Unexpected Cycloannulative Sulfonyl Migration Cascade using (E)-β-Iodovinyl Sulfones and ortho-Alkynylphenols for Direct Synthesis of Chromene-Derived Vinyl Sulfones

Organic Letters, Год журнала: 2023, Номер 25(13), С. 2207 - 2212

Опубликована: Март 29, 2023

Cycloannulative sulfonyl migration has received much attention; however, a carbon-to-carbon group shift still needs to be discovered. We hereby report base-mediated oxa-Michael addition–elimination of (E)-β-iodovinyl sulfones with ortho-alkynylphenols, followed by cycloisomerization and unique stereoselective in one-pot, is realized under the influence Mn(OAc)3·2H2O. A broad range vinyl sulfone-tethered chromenes were readily accessed moderate high yields good functional compatibility. Notably, reaction was robust at gram scale, postsynthetic transformations successfully uncovered. Moreover, plausible mechanistic pathways rationalized on basis existing experimental results.

Язык: Английский

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Formation of 2H- and 4H-chromene Rings in Intramolecular Rauhut–Currier Reaction, Catalyzed by Lithium Selenolates

ACS Omega, Год журнала: 2025, Номер 10(4), С. 3652 - 3664

Опубликована: Янв. 22, 2025

In this paper, we present the first example of using a catalytic amount nucleophilic seleno-organic catalyst in tandem seleno-Michael/Michael reaction, leading to formation 2H/4H-chromenes. Chromenes represent highly significant group oxygen-containing heterocycles commonly found as structural scaffolds diverse range fields such medicinal chemistry, pharmaceutical agents, drug candidates, synthetic and materials chemistry. Various preparation methods have been developed, utilizing different substrates conjunction with metal catalysts, organocatalysts, Brønsted acids, bases, or Lewis acids. The utility lithium selenolates has demonstrated efficient catalysts Rauhut–Currier cyclization chalcone derivatives. This methodology allows for synthesis 2H- 4H-chromenes depending on substituents directly connected carbonyl group. investigation focuses impact various aromatic fragment well conditions selenolates. scope starting was also considered.

Язык: Английский

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Lewis Acid-Mediated Domino Glycosylation/Cyclization of Substituted Glycals: A Stereoselective Route Toward the Synthesis of 1,2-Annulated C-Glycosides

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Март 14, 2025

Annulated C-glycosides are widely recognized for their natural abundance and diverse bioactivity. Traditional synthesis emphasizes stereoselective α/β C-glycoside formation, but efficiently engaging both reactive carbons of glycosyl donors remains challenging. This study introduces a novel domino sequence using substituted glycals β-naphthols under Lewis acid catalysis, generating glycosylated intermediates that undergo cascade reactions to yield annulated 1,2-C-glycosides. The method features broad substrate scope, mild conditions, versatility. Notably, annulation type varies with glycals, yielding [3 + 2] or 3] fused pyran systems. Control experiments DFT calculations provide mechanistic insights into substrate-specific product formation.

Язык: Английский

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Domino syntheses of carbo- and heterocycles from Pd-catalyzed bis-substitutions of allylic bis-carboxylates, -carbonates or –diols

Tetrahedron, Год журнала: 2025, Номер unknown, С. 134680 - 134680

Опубликована: Апрель 1, 2025

Язык: Английский

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K₃PO₄‐Promoted Cycloannulation of (E)‐β‐Iodovinyl Sulfones with ortho‐Hydroxy‐Chalcones/Cinnamates for the Synthesis of 2,3,4‐Trisubstituted 4H‐Benzopyran Derivatives

Advanced Synthesis & Catalysis, Год журнала: 2022, Номер 364(23), С. 4080 - 4087

Опубликована: Окт. 21, 2022

Abstract K 3 PO 4 ‐mediated cycloannulation of ( E )‐β‐iodovinyl sulfones with ortho ‐hydroxy chalcones/ cinnamates has been realized to access 2,3,4‐trisubstituted‐4 H ‐benzopyran derivatives. A metal‐free tandem oxa‐Michael addition and allows the diversity‐oriented synthesis corresponding 3‐sulfonyl‐4 ‐benzopyrans in good high yields. More importantly, one‐pot three‐component reaction between sulfones, 2‐hydroxybenzaldehydes, phosphonium ylides established for ‐chromene derivatives moderate Notably, this process features a broad substrate scope easy elaboration into numerous multifaceted chromene products, including bioactive estrone‐derivative. The present protocol is sustainable at gram scale reactions, post‐synthetic applications were also demonstrated. plausible mechanism presented on basis existing experimental results. magnified image

Язык: Английский

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Synthetic Approaches, Properties, and Applications of Acylals in Preparative and Medicinal Chemistry

Molecules, Год журнала: 2024, Номер 29(18), С. 4451 - 4451

Опубликована: Сен. 19, 2024

Diesters of geminal diols (R-CH(O-CO-R′)2, RR′C(OCOR″)2, etc. with R = H, aryl or alkyl) are termed acylals according to IUPAC recommendations (Rule P-65.6.3.6 Acylals) if the acids involved carboxylic acids. Similar condensation products can be obtained from various other acidic structures as well, but these related “non-classical acylals”, one might call them, differ in aspects classical and will not discussed this article. Carboxylic acid diesters play a prominent role organic chemistry, only their application protective groups for aldehydes ketones also precursors total synthesis natural compounds variety reactions. What is more, useful key structural motif clinically validated prodrug approaches. In review, we summarise syntheses chemical properties such show what potentially under-explored possibilities exist field drug design, especially prodrugs, classify functional group medicinal chemistry.

Язык: Английский

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Total syntheses of carbazole alkaloid mukoenine A and pyrano[3,2-a]carbazole alkaloid girinimbine

Tetrahedron, Год журнала: 2022, Номер 120, С. 132895 - 132895

Опубликована: Июнь 18, 2022

Язык: Английский

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Palladium-catalyzed [4 + 3]-annulations of oxotryptamines with allyl dicarbonates: an approach toward spiro[azepane-4,3′-oxindoles]

Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(18), С. 4593 - 4597

Опубликована: Янв. 1, 2023

A palladium-catalyzed tandem allylic substitution of oxotryptamines with allyl dicarbonates has been developed, affording spiro[azepane-4,3′-oxindoles] in moderate to excellent yields (30%–96%) up >20 : 1 Z -stereoselectivity.

Язык: Английский

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Structurally Divergent Synthesis of Azetidines, 5,6‐Dihydro‐1,3‐oxazines and 2,3‐Dihydro‐1,4‐oxazines through Palladium‐Catalyzed Tandem Allylic Substitution Reaction

Chinese Journal of Chemistry, Год журнала: 2024, Номер 42(22), С. 2773 - 2778

Опубликована: Июль 16, 2024

Comprehensive Summary A regiodivergent synthesis of azetidines, 5,6‐dihydro‐1,3‐oxazines and 2,3‐dihydro‐1,4‐oxazines has been achieved through palladium‐catalyzed tandem allylic substitution reaction. This protocol provides a variety heterocycles in satisfactory yields with good to excellent regioselectivities under mild reaction conditions.

Язык: Английский

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