General Approach to Amides through Decarboxylative Radical Cross-Coupling of Carboxylic Acids and Isocyanides

Organic Letters, Journal Year: 2024, Volume and Issue: 26(16), P. 3380 - 3385

Published: April 12, 2024

Herein, we report a silver-catalyzed protocol for decarboxylative cross-coupling between carboxylic acids and isocyanides, leading to linear amide products through free-radical mechanism. The disclosed approach provides general entry variety of decorated amides, accommodating diverse array radical precursors, including aryl, heteroaryl, alkynyl, alkenyl, alkyl acids. Notably, the proved be efficient late-stage functionalization several elaborate pharmaceuticals, demonstrating its potential applications.

Language: Английский

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Switchable Synthesis of Spirodihydroindolizines and Indolizines from Aurones and Pyridin-2-yl Active Methylene Compounds

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(3), P. 1753 - 1761

Published: Jan. 22, 2024

A novel and flexible domino reaction of aurones with pyridin-2-yl active methylene compounds promoted by I2/BF3 has been developed to afford spirodihydroindolizines indolizines in a controllable manner. When the was performed 1,2-dichloroethane at 80 °C, variety were obtained, whereas it almost exclusively provided series when mixed solvent N,N-dimethylformamide relatively higher temperature 100 °C. Being metal-free, excellent product selectivity, high atom economy, good functional group tolerance, feasibility for large-scale synthesis are salient features methodology.

Language: Английский

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Cu(II)‐Catalyzed [3+2]‐Annulation of 2‐Pyridinyl‐substituted p‐Quinone Methides with Enaminones: Access to Functionalized Indolizine Derivatives

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(19), P. 3271 - 3276

Published: Aug. 17, 2023

Abstract This article describes an effective and atom‐economical protocol to access a wide range of synthetically important functionalized indolizine derivatives. transformation basically takes place through Cu(II) catalyzed formal [3+2] annulation 2‐pyridinyl substituted p ‐quinone methides with enaminones. method displayed good functional group tolerance and, was found be for most the enaminones ‐QMs, corresponding indolizines were obtained in moderate yields.

Language: Английский

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Pd(ii)-catalyzed annulation of terminal alkynes with 2-pyridinyl-substituted p-quinone methides: direct access to indolizines

Chemical Communications, Journal Year: 2022, Volume and Issue: 58(95), P. 13238 - 13241

Published: Jan. 1, 2022

A Pd-catalyzed direct method has been developed to access 1,3-disubstituted indolizines. This reaction proceeds through a regiospecific annulation of terminal alkynes with 2-pyridinyl-substituted p-quinone methides and, in most the cases, desired indolizines were obtained moderate good isolated yields. The control experiments suggested that does proceed substrate-controlled formal [3 + 2]-annulation pathway.

Language: Английский

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Synthesis of Functionalized Indolizines through 1,3-Dipolar Cycloaddition of Zwitterionic Ketenimines and Pyridinium Salts

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

Published: April 19, 2025

A straightforward and efficient strategy for the synthesis of fully functionalized indolizines has been developed through a transition metal- oxidant-free [3 + 2] cycloaddition reaction zwitterionic ketenimines pyridinium salts. This versatile method proceeds under mild conditions, affording in moderate to good yields. approach involves an intermolecular cycloaddition, followed by enamine/imine tautomerization aromatization. Notably, this demonstrates broad functional group compatibility allows facile scalability, making it valuable tool indolizine-based frameworks organic medicinal chemistry.

Language: Английский

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A One-Pot Synthesis of Substituted Pyrrolo[2,1-a]isoquinolines via an Oxidation/Annulation Sequence of 2-(3,4-Dihydroisoquinolin-2(1H)-yl)malononitriles

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

Published: May 15, 2025

A highly effective oxidation/annulation reaction between 2-isocyanoacetates and 2-(3,4-dihydroisoquinolin-2(1H)-yl)malononitriles has been successfully developed to give substituted pyrrolo[2,1-a]isoquinoline derivatives with moderate good yields in a one-pot manner.

Language: Английский

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Recent Applications of Quinolinium Salts in the Synthesis of Annulated Heterocycles

SynOpen, Journal Year: 2022, Volume and Issue: 06(02), P. 86 - 109

Published: April 25, 2022

Abstract Quinoline derivatives are frequently found in natural products and biologically active compounds; however, construction of quinoline fused polyheterocycles is a challenging goal synthetic organic chemistry. In this regard, quinolinium salts meet the demand to great level, as they can be synthesized readily employed effectively for rapid condensed heterocyclic core. The present review focuses on recent (2015–2021) applications different salts, which react with suitable partners access diverse annulated products. Most reactions discussed here involve easily available starting materials, operationally simple, offer high atom-efficiency, environmentally benign. Mechanistic aspects representative transformations have also been highlighted better understand reaction pathways. 1 Introduction 2 Annulation Involving N-Alkyl Quinolinium Salts 2.1 Reaction Alkenes 2.2 Alkynes/Arynes 2.3 Phenolic Compounds 2.4 Cyclic/Acyclic Diketones 2.5 Amines/Cyclic Amines 2.6 Enamines 2.7 Isocyanoacetates 2.8 Cyclopropanes 2.9 Ring Expansion Reactions 3 Zwitterionic Tosylates 3.1 3.2 Allenes/Ketenes 3.3 Aldehyde-Amino Acid (Azomethine Ylide) 3.4 Sulfonium 3.5 Diazoacetate 4 Thiolates 4.1 4.2 Sulfenes 4.3 Arynes 5 N-Oxides 5.1 Diynes Ynones 5.2 Lactonization Acrylate 6 N-Iminoquinolinium 6.1 Allenoates 6.2 Hydroxymethylallyl Carbonate 7 Miscellaneous Cyclizations 8 Conclusions

Language: Английский

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Copper-assisted Wittig-type olefination of aldehydes with p-toluenesulfonylmethyl isocyanide

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 9(15), P. 4158 - 4163

Published: Jan. 1, 2022

A copper-assisted Wittig-type olefination of aldehydes and p -toluenesulfonyl isocyanide (TosMIC) is disclosed, providing an operationally simple approach to ( E )-vinyl sulfone with various functional groups under mild reaction conditions.

Language: Английский

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Construction of Phenanthridinone Skeletons through Palladium-Catalyzed Annulation

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(17), P. 12738 - 12743

Published: Aug. 23, 2023

Herein, a straightforward synthetic approach for the construction of phenanthridin-6(5H)-one skeletons is disclosed. The developed protocol relies on palladium catalysis, providing controlled access to range functionalized phenanthridin-6(5H)-ones in 59-88% yields. Furthermore, plausible reaction pathways are proposed based mechanistic experiments.

Language: Английский

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Domino Approach to Heterocycles-Based Unsymmetrical Triarylmethanes through Heteroannulation of 2-(2-Enynyl)-pyridines with Enaminones

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(17), P. 12104 - 12117

Published: Aug. 13, 2024

Herein, we report a copper-catalyzed protocol to access unsymmetrical triarylmethanes containing both indolizine and the chromone scaffolds in same molecule via 5-endo-dig cyclization of 2-(2-enynyl)-pyridines followed by reaction with 2-hydroxyaryl enaminones. A variety enaminones were subjected under optimal conditions, respective obtained good excellent yields.

Language: Английский

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