Carbene-Catalyzed [3 + 3] Annulation of Enals and Vinyl Sulfoxonium Ylides DOI

Siru Feng,

Hailong Zhang, Jinhua Liu

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 25, 2024

Carbene-catalyzed [3 + 3] annulation of enals and vinyl sulfoxonium ylides has been demonstrated. This method efficiently synthesizes a range 2-sulfenylidene-3-cyclohexen-1-ones with high atom economy. Notably, the presence ylide moiety in obtained products significantly enhances their potential for further synthetic transformations.

Language: Английский

Condition‐Controlled Selective Synthesis of CF3‐Chromene and CF3‐Benzofuran from N‐Phenoxyacetamide and CF3‐Ynone DOI Open Access

Huihang Hou,

Shengnan Yan,

Yuanshuang Xu

et al.

Chinese Journal of Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: March 27, 2025

Comprehensive Summary Presented herein is a condition‐controlled selective synthesis of CF 3 ‐chromene and ‐benzofuran based on the reaction N ‐phenoxyacetamide ‐ynone. When carried out in MeOH under catalysis Rh(III), formed via C—H metalation‐initiated alkenylation, acetamide group migration intramolecular oxo ‐nucleophilic addition. On other hand, when run DMSO promotion CsOAc, generated aza ‐Michael addition‐initiated [3,3]‐σ rearrangement, addition water elimination. To our knowledge, this first report construction chromene or benzofuran scaffold along with introduction unit from same starting materials. The methodology was scalable products could be readily transformed into valuable products. Moreover, thus obtained possess decent anticancer activity.

Language: Английский

Citations

1
Construction of Diverse Fused Chromene Frameworks via Isocyanide-Based Three-Component Reaction DOI

Yu‐Wei He,

Li Huang, Kun Huang

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(15), P. 10854 - 10866

Published: July 12, 2024

A convenient synthetic protocol for diverse fused chromenes was successfully developed by a three-component reaction of alkyl isocyanides, dialkyl but-2-ynedioates, and various cyclic 1,3-dipolarophiles containing

Language: Английский

Citations

5
Ylide-Induced Ring Contraction of Coumarins to Benzofurans: Applications to the Synthesis of Bis-Heterocycles DOI
Sandeep Kumar,

Dinesh Kumar Gopalakrishnan,

Shashank Shrotriya

et al.

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

Published: Feb. 15, 2025

We report an unusual ring contraction of 4-chlorocoumarin to benzofuranoyl sulfoxonium ylides using a Corey-ylide. These stabilized were subsequently utilized for the synthesis various valuable bis-heterocycles under both metal and metal-free conditions. The synthetic utility this method is illustrated through known bioactive compounds. Detailed mechanistic investigations quantum chemical calculations have provided insights into mechanism reaction.

Language: Английский

Citations

0
Asymmetric Synthesis of Chiral Cyclopropanes from Vinyl Sulfoxonium Ylides Catalyzed by a Chiral-at-Metal Rh(III) Complex DOI

Xiaoting Xie,

Zhifei Zhao,

Jun Wang

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 17, 2024

A chiral-at-metal Rh(III) complex-mediated [2+1] cyclization of vinyl sulfoxonium ylides with α,β-unsaturated 2,2-acylimidazoles has been demonstrated for the first time. This work provides a practical approach assembling 1,2,3-trisubstituted chiral cyclopropane alkyl structural units, which had advantages such as wide range substrates, good functional group tolerance, and mild reaction conditions. In addition, further amplification experiments transformation cycloaddition products were carried out to highlight practicality method.

Language: Английский

Citations

2
Regioselective Synthesis of N-Aryl Pyrazoles from Alkenyl Sulfoxonium Ylides and Aryl Diazonium Salts DOI

Ramesh Kumar Vishwakarma,

Raju Sen,

Shalu Deshwal

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 2, 2024

A convenient and practical method has been developed for synthesizing various N-aryl pyrazoles from vinyl sulfoxonium ylides diazonium salts. When using 1,3-disubstituted ylides, the reaction selectively yields 1,3,5-trisubstituted pyrazoles. On other hand, employing 2,3-disubstituted results in formation of 1,3,4-trisubstituted The proceeds through novel aryl diazene-derived ylide. Furthermore, this efficiently produces aniline derivatives a one-pot transformation. takes place under transition metal-free, mild conditions easily accessible starting materials, making it approach generating pharmaceutical chemistry.

Language: Английский

Citations

2
Diastereoselective Cyclopropanation of α,β- Unsaturated Carbonyl Compounds with Vinyl Sulfoxonium Ylides DOI

Shalu Deshwal,

Dinesh Kumar Gopalakrishnan,

Alok Purohit

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(31), P. 6294 - 6307

Published: Jan. 1, 2024

Vinyl cyclopropane scaffolds were synthesized via a proline-catalysed multicomponent reaction involving vinyl sulfoxonium ylides, aldehydes, and indane 1,3-dione.

Language: Английский

Citations

1
Base-Promoted Chemodivergent Construction of 2H-Chromen-2-one and Chromeno[2,3-c]pyrrole Scaffolds from para-Quinone Methides and α-Alkylidene Succinimides DOI

Km Roshani,

Mohammad Saim Raza,

Rama Krishna Peddinti

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(42), P. 9114 - 9119

Published: Oct. 11, 2024

Herein, we evolve a base-promoted synthesis of 2

Language: Английский

Citations

1
Nucleophilic Dearomatization of Activated Pyridines Using Vinyl Sulfoxonium Ylides: Application to the Synthesis of Bis-Heterocycles DOI

Srashti Bhardwaj,

Dinesh Kumar Gopalakrishnan,

Tarak Karmakar

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 5, 2024

A highly efficient method has been developed for synthesizing 4-dienyl dihydropyridines through the nucleophilic dearomatization of activated pyridines using vinyl sulfoxonium ylides. This reaction follows sequence involving ylide addition to pyridine, [2,3]-sigmatropic rearrangement, and subsequent sulfenic acid elimination. The resulting are then used in synthesis substituted bis-heterocyles. Control experiments quantum chemical calculations were conducted elucidate selectivity mechanistic pathway.

Language: Английский

Citations

1
K<sub>3</sub>PO<sub>4</sub>–Mediated Synthesis of Chromeno–[3,4‐<i>c</i>]isoxazole From 3–Nitro–2<i>H</i>–chromene and <i>α</i>–Chloro Aldehyde via Michael addition/C–Cl bond cleavage/deformylation as Key Fragmentation Sequences DOI

Aniruddh Pratap,

Pushpendra Mani Shukla,

Santanab Giri

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(19), P. 4122 - 4131

Published: July 12, 2024

Abstract Here we report a transition metal– and oxidant–free annulation cascade method for the synthesis of chromeno–isoxazoles. The reaction involves easily accessible starting materials, 3‐nitro‐2 H ‐chromene α ‐chloro aldehyde, yielding structurally intriguing framework, chromeno[3,4‐ c ]isoxazoles employed by tripotassium phosphate as base. isoxazole ring construction over 2 –chromene unit is believed to occur via series multiple sequences. Here, enolate generation/Michael addition/C−Cl bond cleavage/oxy–anionic addition reactive tethered‐aldehyde/deformylation retro–C−C N−O cleavages are most possible sequences which furnish desired end–product in good chemical yields. one‐pot at mild conditions, supported experimental results few control experiments including DFT studies. This process exhibits broad substrates scope illustrating functional group compatibility towards both nitrochromenes aldehydes, thus prove be general efficient protocol chromeno[3,4– ]isoxazoles. Overall, use nitrochromene limiting reagent, noteworthy tolerance, scalability great applications like chiral pool strategy enantioenriched chromeno‐isoxazole additional features.

Language: Английский

Citations

0
Solvent-involved synthesis of pyrrolidin-5-one-2-carboxamides via a sequential Ugi/olefination reaction DOI
Na Chen,

Tianyu Long,

Han‐Han Kong

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(10), P. 2780 - 2785

Published: Jan. 1, 2024

An unprecedented multi-component reaction with solvent participation and a novel conversion of sulfur ylides was developed via Ugi/olefination to construct pyrrolidin-5-one-2-carboxamides.

Language: Английский

Citations

0