Progression on Oxidative Decyanation Approaches from Secondary Nitriles to Ketones and α‐Aminonitriles to Amides DOI Open Access

Swetha Sathyendran,

Gopal Chandru Senadi

Asian Journal of Organic Chemistry, Год журнала: 2023, Номер 12(11)

Опубликована: Сен. 27, 2023

Abstract The functional group transformation associated with nitrile moiety is considered a diligent research topic in the synthetic community as it building block for several organic molecules, including ketones and amides. Many methodologies have been developed synthesizing amides, considering them analogues exciting biological properties. However, there are limited articles to synthesize these important classes of compounds via oxidative decyanation nitriles α‐aminonitriles. As protocols decyanation, base‐induced functionality oxo carbanion formation an effective but under‐explored area research. In this context, we wish present outline studies secondary α‐aminonitriles afford corresponding amides since its inception.

Язык: Английский

Shaking Up the Friedländer Reaction: Rapid, Scalable Mechanochemical Synthesis of Polyaryl‐substituted Quinolines DOI
Daliah Farajat, Jean‐Louis Do, Pat Forgione

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер unknown

Опубликована: Авг. 16, 2024

Abstract Quinolines are ubiquitous heterocyclic aromatic scaffolds, which can be found in many natural and synthetic products. They highly valued for their pharmacological electrochemical properties, encouraging the discovery of new routes quinoline synthesis diversification. In particular, polyaryl‐substituted quinolines have recently surged as useful substrates a wide variety applications, yet remain difficult inefficient. Herein, we report rapid novel mechanochemical Friedländer under basic conditions using ball milling. The optimized reaction resulted moderate to excellent yields ranging from 48% >95% demonstrated broad functional group tolerance at 1 hour times. We further show route photocatalyst DPQN 2,4−di−OMe photo‐ligand PPQN well OLED donor‐acceptor pCzPPQ, electron transport material oligoquinoline TQB organic semiconductor DPA. A gram scale was also achieved Resonant Acoustic Mixing (RAM), providing an isolated yield 87% after simple recrystallization ethanol.

Язык: Английский

Процитировано

4

Photoredox Radical Cyclization of o-Vinylaryl Isocyanides and Aryldiazonium Tetrafluoroborates for the Synthesis of 2,4-Disubstituted Quinolines DOI
Min Gao, Chuan Ding, Peng‐Fei Huang

и другие.

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Март 23, 2025

Quinolines, a significant part of nitrogen-containing heterocycles, are widely found in functional compounds. Herin, photochemical radical cyclization reaction o-vinylaryl isocyanides and aryldiazonium tetrafluoroborates, has been reported to build 2,4-diaryl quinolines. Readily accessible aryl diazonium salts were utilized as precursors at room temperature. This approach allowed good group tolerance substrate applicability.

Язык: Английский

Процитировано

0

Development of a Recyclable GO-Metformin-Pd(0) Nanocatalyst for Ecofriendly Synthesis of Quinoline-4(1H)-ones and Flavones via Multicomponent-Carbonylation Reactions DOI
Mosstafa Kazemi, Vicky Jain,

Suhas Ballal

и другие.

Journal of Organometallic Chemistry, Год журнала: 2025, Номер unknown, С. 123699 - 123699

Опубликована: Май 1, 2025

Язык: Английский

Процитировано

0

Iron-catalyzed formation of six-membered rings from alkyne DOI Creative Commons
Hui Li,

Sang I. Yi,

Chunling Zeng

и другие.

Green Synthesis and Catalysis, Год журнала: 2025, Номер unknown

Опубликована: Май 1, 2025

Язык: Английский

Процитировано

0

Fe‐Catalyzed, Solvent‐Controlled, Switchable Routes for the Domino Construction of 2,4‐Disubstituted and 4‐Substituted Quinoline Scaffolds DOI Open Access
Prafull A. Jagtap, Vaishnavi R. Sawant, Bhalchandra M. Bhanage

и другие.

ChemCatChem, Год журнала: 2024, Номер unknown

Опубликована: Июль 27, 2024

Abstract In this report, we unveil a highly efficient novel protocol for the domino synthesis of 2,4‐disubstituted and 4‐substituted quinoline scaffolds. The developed strategy involves earth‐abundant Fe‐catalyzed, solvent‐controlled, switchable routes selective construction frameworks, achieved by using either trifluoroethanol (TFE) or methanol (MeOH) as solvent. By employing TFE solvent in Path A, alkyne itself serves dual synthon through Fe‐catalyzed situ C( sp )–C( ) bond cleavage, enabling two important molecules: quinolines. Later, upon switching reaction medium from to MeOH Path‐B, only quinolines were obtained extensively. oxidation was observed here functioned both an environmentally benign carbon source. Both these strategies utilized prepare broad range mono‐ di‐substituted derivatives. application section practical utility, scale‐up studies, along with photophysical properties synthesized moiety are also demonstrated.

Язык: Английский

Процитировано

1

Lewis Acid Catalyzed [4 + 2] Annulation of Propargylic Alcohols with 2-Vinylanilines DOI

Xi-Yan Ren,

Xiang‐Xuan Feng,

Hong‐Yu Zhang

и другие.

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(22), С. 16007 - 16017

Опубликована: Окт. 31, 2023

An elegant Lewis acid catalyzed, protection-free, and straightforward synthetic strategy for the assembly of a series sophisticated polycyclic quinoline skeletons employing propargylic alcohols 2-vinylanilines as substrates in presence Yb(OTf)3 (10 mol %) AgOTf tetrahydrofuran has been described. This annulation protocol, which proceeds through sequential Meyer-Schuster rearrangement/nucleophilic substitution/deprotonation sequence, provides versatile, practical, atom-economical approach accessing derivatives moderate-to-good yields.

Язык: Английский

Процитировано

3

Progression on Oxidative Decyanation Approaches from Secondary Nitriles to Ketones and α‐Aminonitriles to Amides DOI Open Access

Swetha Sathyendran,

Gopal Chandru Senadi

Asian Journal of Organic Chemistry, Год журнала: 2023, Номер 12(11)

Опубликована: Сен. 27, 2023

Abstract The functional group transformation associated with nitrile moiety is considered a diligent research topic in the synthetic community as it building block for several organic molecules, including ketones and amides. Many methodologies have been developed synthesizing amides, considering them analogues exciting biological properties. However, there are limited articles to synthesize these important classes of compounds via oxidative decyanation nitriles α‐aminonitriles. As protocols decyanation, base‐induced functionality oxo carbanion formation an effective but under‐explored area research. In this context, we wish present outline studies secondary α‐aminonitriles afford corresponding amides since its inception.

Язык: Английский

Процитировано

1