Divergent Synthesis of Polysubstituted 1,2-Dihydropyridines and Pyridines through Manganese-Mediated Radical Cascade Cyclization of Tertiary Enamides

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

Published: Jan. 28, 2025

A Mn(III)-mediated radical cascade cyclization of N-propargyl enamides with sodium sulfinates was developed. Mechanistic studies indicated that this process is mainly composed the chemoselective addition sulfonyl to C≡C bond and regioselective intramolecular 6-endo-trig cyclization. This protocol provided a powerful method for divergent synthesis diverse polysubstituted meta-sulfonylpyridines or 1,2-dihydropyridines just by varying solvent temperature featuring good functional group compatibility simple operation.

Language: Английский

---

Three-Component Sulfonylation and Heteroannulation Enabled by 3-Fold Defluorofunctionalization of Trifluoromethyl Enones

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

Published: Feb. 23, 2025

Trifluoromethyl enone emerges as a versatile and multifaceted building block in organic synthesis. A defluorinative heterocyclization reaction of readily available β,β-ditrifluoromethylated enones biocompatible sodium sulfinates has been developed for the modular synthesis densely functionalized furans with regio-defined C2,4-bissulfonyl C3-trifluoromethyl substitutions. This three-component method proceeds through sequential sulfonylation intramolecular O-cyclization, enabling assembly one furan ring, formation C-SO2/C–O bonds, cleavage three C(sp3)-F bonds one-pot manner under transition metal-free conditions. Moreover, obtained product can further react benzyne precursor to generate 1,4-epoxynaphthalene Diels–Alder cycloaddition. The is also distinguished by its broad substrate scope, excellent functional group tolerance, scalability.

Language: Английский

---

Synthesis of 2-Sulfonyl Carbazoles via Oxidative C–H Functionalization of Tetrahydrocarbazoles with Sulfonyl Hydrazides

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 11, 2025

Herein, we report an approach for the synthesis of 2-sulfonyl carbazoles from oxidative C–H sulfonylation tetrahydrocarbazoles. The mechanistic study reveals that this special selectivity is realized by addition a sulfonyl radical to 3,4-dihydrocabazole intermediate via dehydrogenative desaturation This features readily available starting materials, high regioselectivity, broad substrate scope, and attractive synthetic utility.

Language: Английский

---

Visible-Light-Induced Sulfonylation Cyclization to Generate Indole-Fused Medium-Sized N-Heterocycles in 2-Me-THF

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

Published: Feb. 27, 2025

A novel visible-light-induced sulfonylation cyclization to indole-fused medium-sized N-heterocycles was established under room temperature with biomass-derived 2-Me-THF as the solvent. This reaction proceeds in absence of external photocatalyst, additive, metal salts, and base. Broad substrate scope, good functional group compatibility, large-scale synthesis derivatization via iodination, nitration, chlorination, cyanation, selenylation demonstrate utility this protocol. radical route proposed based on inhibition experiments, visible-light irradiation on-off test, apparent quantum efficiency calculation, UV-vis absorption spectroscopic studies.

Language: Английский

---

Catalyst- and Solvent-Free Hydrosulfonylation of Alkenes with Sulfinates Enabling Green Synthesis of β-Sulfonyl Amides

Tetrahedron, Journal Year: 2025, Volume and Issue: unknown, P. 134632 - 134632

Published: March 1, 2025

Language: Английский

---

Access to C5-Sulfonylated Tetrahydropyridazines via Photoinduced Cascade Sulfonylation-Cyclization of N-Cinnamyl Aldehyde Hydrazones

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

Published: April 15, 2025

Direct installation of a sulfonyl functional group into the C5-position tetrahydropyridazine was achieved using N'-benzylidene-N-cinnamylacetohydrazide as new building skeleton via photocatalytic carbosulfonylation/annulation procedure. Various substituted C5-sulfonylated tetrahydropyridazines were obtained in good to excellent yields employing aryl- or alkylsulfonyl chlorides radical sources. This reaction realized through selective addition C2 position cinnamyl followed by 6-endo-trig annulation hydrazone CH═N bond.

Language: Английский

---

Sustainable Approaches for the Synthesis of Functionalized Xanthene Derivatives with Anticancer Activities Using Modern Green Tools at Room Temperature: Less Energy and More Efficiency

Synlett, Journal Year: 2025, Volume and Issue: unknown

Published: April 30, 2025

Abstract Functionalized xanthenes occupy an important position in medicinal chemistry due to their wide range of pharmacological properties. The xanthene skeleton is present various bioactive natural products such as mulgravanols A and B, hermannol, (+)-myrtucommulone D, homapanicones blumeaxanthene II, acrotrione, etc. Important xanthene-based drugs, including propantheline bromide, methantheline, phloxine etc., are available on the market. Thus, much effort has been dedicated generating or modifying crucial O-heterocyclic compounds. Recently, development efficient processes for synthesis derivatives using modern techniques received significant attention overcome disadvantages traditional methodologies. Aligned with sixth principle green chemistry, which minimum energy needed perform synthetic methods at ambient temperature optimum productivity, this account focuses green, room-temperature strategies anticancer activities 1 Introduction 2 Synthesis Xanthene Derivatives through Green Strategies Room Temperature 3 Medicinal Perspectives Anticancer Agents 4 Conclusion 5 List Abbreviations

Language: Английский

---

Iron-Catalyzed Alkylative Aminosulfonylation of Alkenes and Alkynes via Radical-Anion Relay

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: May 19, 2025

A novel Fe-catalyzed alkylative aminosulfonylation of alkenes and alkynes with alkyl halides O-Ts activated hydroxylamines by using Na2S2O4 as a reductant sulfone source has been developed. The metal-electron-shuttle catalysis was discovered to be vital for the highly efficient generation sulfonyl radicals anions without requiring organometallic intermediates. This method provides access sulfonamides from easily available features broad substrate scope.

Language: Английский

---

Visible-Light-Induced Radical 1,3-Hydrosulfonylation of Allylketones with Sulfonyl Chlorides

Chemical Communications, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

A radical 1,3-hydrosulfonylation of allylketones with sulfonyl chlorides via 1,2-carbonyl migration has been achieved under visible-light-irradiation.

Language: Английский

---

Reactivity Tuning for Selective Aldimino-Sulfonylation of Styrenes by Photocatalytic Activation of Sulfonyl Aldimines

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

Published: May 31, 2025

Imino-sulfonylation of styrene represents a powerful method for constructing highly functionalized molecules, while only diphenyl imines were able to be employed in previous reports. By modulating the electron property styrene, visible-light-mediated radical/radical cross-coupling aldiminyl radical and carbon-centered was achieved synthesize diverse aldimine-embedded sulfones by using sulfonyl aldimines α-trifluoromethylstyrenes. One-pot oxidation delivered Ritter-type amidation products without need excessive nitriles as solvent. Furthermore, this protocol took advantage simple reaction conditions, good substituent diversity, high atom economy broaden research radicals amination alkenes.

Language: Английский

---