Sustainable Synthesis of Polyfluoro-Pyrimido [1,2-a] Benzimidazole Derivatives Using a Tandem Strategy─Ultrasound and an Integrated Continuous Flow System

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

Published: March 6, 2025

We have developed a novel ultrasound technique that generates significant amounts of CF3-substituted benzo[4,5] imidazo [1,2-a]pyrimidine analogues from easily accessible starting materials in an ecologically friendly and efficient approach. This method is notably helpful for producing physiologically relevant compounds containing the imidazopyrimidine unit, which serves as versatile building block synthesis N-fused heterocycles devoid metals, solvents, additives, catalysts. Additionally, utilizing open-air environment, range polyfluoro-ynones were successfully reacted with 2-aminobenzimidazole, generating diverse array polyfluoroimidazo[1,2-a]pyrimidine derivatives. Furthermore, by employing integrated flow system approach, we able to synthesize polyfluoro-substituted benzo[4,5]imidazo[1,2-a]pyrimidine derivatives alkynes much shorter reaction time. Gram-scale proved this method's scalability highlighted its potential synthetic industrial applications. The straightforward nature process, broad compatibility various functional groups, substantial sustainability advantages collectively underscore significance.

Language: Английский

Recent Advances in Transition‐Metal Catalyzed Synthesis of N‐Heterocycles using Solvent‐Carbon (C1) Synthons

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

Mechanism and Optimization of Ruthenium-Catalyzed Oxalamide Synthesis Using DFT

Dalton Transactions, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 6, 2024

The oxalamide skeleton is a common structural motif in many biologically active molecules. These scaffolds can be synthesized

Language: Английский