Synthesis of α-Carbonyl-α′-amide Sulfoxonium Ylides from Isocyanates with Complete Atom Economy

Organic Letters, Journal Year: 2023, Volume and Issue: 25(7), P. 1214 - 1217

Published: Feb. 9, 2023

An efficient catalyst- and additive-free facile synthesis of α-carbonyl-α′-amide sulfoxonium ylides from isocyanates β-ketosulfoxonium with complete atom economy has been described. The adorned various functional groups were well-tolerated afforded moderate to high yields the ylide derivatives. Finally, using large-scale reactions converting synthesized into other valuable compounds, we demonstrated practicality this synthetic method.

Language: Английский

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Recent advance: Sulfur ylides in organic synthesis

Journal of Heterocyclic Chemistry, Journal Year: 2023, Volume and Issue: 61(1), P. 29 - 70

Published: Oct. 26, 2023

Abstract Sulfur ylides are versatile structures that display various characteristics and participate in a myriad of reactions to produce simple, effective, sometimes stereoselective toward synthesizing sulfur‐containing compounds. Nonetheless, their fulfillment tremendous developments have been made this field the past few decades. In comprehensive review, luminosity is illuminated on application sulfur involved domino, cascade annulation reactions, carbene trapping reagents with chameleonic reactivity. numerous decennary, chemists used solvent‐dependent, rhodium catalyzed, dealkylative intercepted, photochemical reaction, halotrifluoromethylation, benzannulation, amidation name such as Mizoroki–Heck, Suzuki–Miyaura, Sommelet–Hauser rearrangements. Moreover, other prime applications include metal catalysis, epoxidation carbonyl compounds, acylmethylation, cyclomerization, oxidation, insertion reactions. Additionally, some extremely useful play major role synthesis medicinally active heterocycles structural motifs. This review article discusses all these proposed mechanisms, current scenario, at length. tutorial concludes by providing future outlook investigation into compounds synthesized using it great potential be industries, laboratories, pharmaceutical companies, drug production, clinical use, medicinal chemistry, agrochemical purposes.

Language: Английский

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Direct C−H Sulfuration: Synthesis of Disulfides, Dithiocarbamates, Xanthates, Thiocarbamates and Thiocarbonates

Chemistry - An Asian Journal, Journal Year: 2024, Volume and Issue: 19(9)

Published: Feb. 29, 2024

Abstract In light of the important biological activities and widespread applications organic disulfides, dithiocarbamates, xanthates, thiocarbamates thiocarbonates, continual persuit efficient methods for their synthesis remains crucial. Traditionally, preparation such compounds heavily relied on intricate multi‐step syntheses use highly prefunctionalized starting materials. Over past two decades, direct sulfuration C−H bonds has evolved into a straightforward, atom‐ step‐economical method organosulfur compounds. This review aims to provide an up‐to‐date discussion disulfuration, dithiocarbamation, xanthylation, thiocarbamation thiocarbonation, with special focus describing scopes mechanistic aspects. Moreover, synthetic limitations some these methodologies, along key unsolved challenges be addressed in future are also discussed. The majority examples covered this accomplished via metal‐free, photochemical or electrochemical approaches, which alignment overraching objectives green sustainable chemistry. comprehensive consolidate recent advancements, providing valuable insights dynamic landscape strategies crucial classes

Language: Английский

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Electro-Oxidative Three-Component Synthesis of 3,5-Disubstituted-1,2,4-Thiadiazoles from Amines, Amidines, and CS₂

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

Published: March 29, 2025

1,2,4-Thiadiazoles, a significant class of heterocyclic compounds, are widely found in biologically active molecules. Herein, we report green electrochemical three-component reaction amines, amidines, and CS2 for the effective synthesis 3,5-disubstituted-1,2,4-thiadiazoles under metal- oxidant-free conditions. Both aliphatic aryl amines well-tolerated at room temperature simple undivided cell. A series 1,2,4-thiadiazoles prepared with excellent functional groups.

Language: Английский

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Straightforward access to α-thiocyanoketones and thiazoles from sulfoxonium ylides

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(68), P. 10247 - 10250

Published: Jan. 1, 2023

Efficient, versatile, and metal-free strategies for synthesizing α-thiocyanoketones thiazoles from β-ketosulfoxonium ylides ammonium thiocyanate have been described. Due to its simplicity, benign reaction conditions, excellent chemoselectivity, high yield, this method represents a unique approach divergent synthesis. Finally, the potential value of developed methods is demonstrated via large-scale reactions synthesis Fanetizole, an anti-inflammatory drug.

Language: Английский

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Multicomponent Reaction of CS₂, Amines, and Sulfoxonium Ylides in Water: Straightforward Access to β-Keto Dithiocarbamates, Thiazolidine-2-thiones, and Thiazole-2-thiones

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(9), P. 6120 - 6125

Published: April 5, 2023

Simple, versatile, and catalyst-free synthetic methods for β-keto dithiocarbamates, thiazolidine-2-thiones, thiazole-2-thiones via the multicomponent reaction of CS2, amines, sulfoxonium ylides have been described. The furnished dithiocarbamates in presence CS2 secondary whereas primary amines afforded thiazolidine-2-thiones or after dehydration an acidic environment. With simple procedures, has a wide substrate scope excellent functional group tolerance.

Language: Английский

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Annulative coupling of α-substituted acrylic acids and sulfoxonium ylides: Easy access to bioactive γ-butyrolactones

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(67), P. 8872 - 8875

Published: Jan. 1, 2024

We present a straightforward, catalyst- and additive-free method for synthesizing keto γ-butyrolactones using readily available β-keto sulfoxonium ylides acrylic acids. This robust approach demonstrates exceptional compatibility with various functional groups on α-substituted acids, resulting in good to high yields of the anticipated products. Moreover, practicality this was validated through large-scale reactions successful conversion some synthesized derivatives into bioactive natural products, including L-factor, muricatacin, cytosporanone A.

Language: Английский

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Base-mediated synthesis of cyclic dithiocarbamates from 1-amino-3-chloropropan-2-ol derivatives and carbon disulfide

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(31), P. 6293 - 6297

Published: Jan. 1, 2023

An efficient method for the preparation of six-membered cyclic dithiocarbamates is described, in which triethylamine effectively promotes reaction 1-amino-3-chloropropan-2-ol derivatives with carbon disulfide. On basis experimental and theoretical studies, a mechanism proposed to explain difference between present our previously reported dioxide fixation.

Language: Английский

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Visible-light Induced Decarboxylative Coupling of Phenoxyacetic Acid with Disulfides: Synthesis of α-Arylthioanisole Derivatives

Chemical Communications, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

Photoredox-catalyzed cross-coupling reaction is an efficient strategy for the construction of organic molecules.

Language: Английский

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Acylation of Electron-Poor Alkenyl Sulfoxides: Diverse Transformations for the Synthesis of Polysubstituted Phenols and Functionalized Carbocycles

Synthesis, Journal Year: 2023, Volume and Issue: 55(17), P. 2674 - 2682

Published: May 15, 2023

Abstract A protocol with available starting materials and mild conditions was developed for the synthesis of polysubstituted phenols functionalized carbocycles via acylation electron-poor alkenyl sulfoxides. The plausible mechanism investigated.

Language: Английский

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