Synthesis of Isoquinolone, 1,2-Benzothiazine, and Naphtho[1′,2′:4,5]imidazo[1,2-a]pyridine Derivatives via Rhodium(III)-Catalyzed (4 + 2) Annulation DOI

Yueyue Zhu,

Rupeng Dai,

Chaoqun Huang

et al.

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(17), P. 11722 - 11734

Published: Aug. 15, 2022

In this study, we report a novel and efficient synthetic method to construct isoquinolone scaffold via the Rh(III)-catalyzed (4 + 2) annulation of benzamide with an unreported coupling reagent methyl 2-chloroacrylate. Accordingly, other valuable 1,2-benzothiazine naphtho[1′,2′:4,5]imidazo[1,2-a]pyridine derivatives are also obtained through similar protocol. Thus, our developed is highlighted by high yield reaction versatility.

Language: Английский

Dual Role of (NH4)2CO3 Enables Defluorinative Synthesis of β-Fluoroalkylated Aminovinyl Ketones DOI
Yulan Chen, Wei Han,

Man-Hang Feng

et al.

Organic Letters, Journal Year: 2022, Volume and Issue: 24(49), P. 9086 - 9091

Published: Dec. 2, 2022

A modular multicomponent reaction of readily available fluoroalkyl alkenes, amidines, ammonium carbonate, and water was developed for the facile construction β-fluoroalkylated aminovinyl ketones, which provided chemists a novel access to value-added organofluorine compounds. The proceeded regio-/stereoselectively under mild conditions exhibited good functional group tolerance. Cheap, stable, low-toxic inorganic salt (NH4)2CO3 first found act as both nitrogen source carbonyl equivalent in multi-bond-forming process.

Language: Английский

Citations

13

Recent Advances in Transition‐Metal Catalyzed Synthesis of N‐Heterocycles using Solvent‐Carbon (C1) Synthons DOI
Karthick Govindan, Alageswaran Jayaram,

Vijay Thavasianandam Seenivasan

et al.

ChemCatChem, Journal Year: 2024, Volume and Issue: unknown

Published: May 27, 2024

Abstract Nitrogen‐containing heterocycles represent fundamental components found in a myriad of natural compounds, pharmaceuticals, tailored bioactive substances, and agrochemicals. In recent decades, the field synthetic chemistry has prioritized these directing considerable research endeavour toward developing efficient concise methodologies for their synthesis. Consequently, there is growing interest pioneering novel approaches to fabricate immensely coveted structural motifs. Transition metal‐catalyzed reactions leveraging solvents as carbon (C1) synthons offer notable advantages, including streamlined processes, enhanced atom economy, environmental sustainability. This review sheds light on advancements utilization collective such methanol (alongside other alcohols), N,N ‐dimethylethanolamine (DMEA), triethylamine (TEA) (in conjunction with amines), tetrahydrofuran (THF), toluene, dichloromethane (DCM), dimethyl sulfoxide (DMSO), dimethylformamide (DMF) C1 synthons, serving foundational units synthesis N ‐heterocycles, quinazolinone, quinazoline, quinoxaline, pyridine, pyrimidine, among others. Various reaction conditions employing diverse transition metals, coupling partners, or reagents, reported literature, have been explored.

Language: Английский

Citations

2

Rh‐catalyzed three‐component synthesis of diverse N‐aryl pyrazoles via cascade pyrazole annulation and aryl C‐H addition to alkenes DOI

Xinyuan Wen,

Jie‐Ping Wan, Ming Zhang

et al.

Applied Organometallic Chemistry, Journal Year: 2024, Volume and Issue: 38(9)

Published: July 5, 2024

A novel Rh‐catalyzed three‐component synthesis of N ‐( o ‐alkylaryl) pyrazoles via cascade pyrazole annulation and aryl C‐H conjugate addition to alkenes has been developed with enaminones, hydrazines, functionalized as starting materials. The raw materials used in this reaction are simple, cheap, readily available, the reactions feature excellent step economy by furnishing products formation a ring key activation one‐step operation. Moreover, proceeds smoothly under air atmosphere, making it easy operate.

Language: Английский

Citations

2

Tandem site-selective bromination and highly regioselective Heck reaction of N-allyl enaminones: chemodivergent synthesis of polysubstituted pyrroles and pyridines DOI
Xiyan Duan, Junqi Wang, Huijun Li

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(19), P. 5532 - 5537

Published: Jan. 1, 2024

Chemodivergent synthesis of polysubstituted pyrroles and pyridines from N -allyl enaminones via tandem site-selective bromination the highly regioselective Heck reaction.

Language: Английский

Citations

2

Synthesis of Isoquinolone, 1,2-Benzothiazine, and Naphtho[1′,2′:4,5]imidazo[1,2-a]pyridine Derivatives via Rhodium(III)-Catalyzed (4 + 2) Annulation DOI

Yueyue Zhu,

Rupeng Dai,

Chaoqun Huang

et al.

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(17), P. 11722 - 11734

Published: Aug. 15, 2022

In this study, we report a novel and efficient synthetic method to construct isoquinolone scaffold via the Rh(III)-catalyzed (4 + 2) annulation of benzamide with an unreported coupling reagent methyl 2-chloroacrylate. Accordingly, other valuable 1,2-benzothiazine naphtho[1′,2′:4,5]imidazo[1,2-a]pyridine derivatives are also obtained through similar protocol. Thus, our developed is highlighted by high yield reaction versatility.

Language: Английский

Citations

8