Green Synthesis of 1,4-Dihydropyridines through Catalyst-Free Multicomponent Hantzsch Reaction in an Undergraduate Teaching Laboratory

Journal of Chemical Education, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 27, 2025

Multicomponent reactions (MCRs) are fascinating chemical processes where three or more starting materials come together to form a single product. By exploring various MCRs, second-year undergraduate students learn about the synergy between different functional groups and how they influence reactivity, power of streamlined approach compared conventional stepwise reactions, critical thinking MCR mechanisms. Herein, we introduce valuable synthetic method for constructing heterocyclic compounds through multiple-component condensation/cycloaddition process. Specifically, focus on 1,4-dihydropyridine (1,4-DHP), privileged N-heterocyclic scaffold widely used in medicinal chemistry, particularly 4-aryl-3,5-dicarboxylated derivatives. The experiment provides an excellent opportunity explore concept green chemistry while synthesizing structurally interesting useful molecules using readily available materials. achieve this condensation reaction 2-furaldehyde (furfural), acetoacetic acid tert-butyl ester, ammonium acetate. Key features teaching include following. (1) reaction: involves concise, multicomponent with short time. (2) Catalyst-free: Notably, proceeds without need solvents catalysts. (3) Visually striking system: change system is visually evident, enhancing learning experience. (4) Useful methodology drug synthesis: has practical implications synthesis. We successfully implemented proposal across five parallel student groups, involving approximately 150 participants. experimental procedures encompass organic synthesis, thin-layer chromatography (TLC), nuclear magnetic resonance (NMR) analysis.

Language: Английский

Photoredox-enabled ring-opening of cyclobutanes via the formation of a carbon radical

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(17), P. 4663 - 4670

Published: Jan. 1, 2024

The high strain energy of cyclobutanes has been utilized for selective ring-opening, enabling the synthesis valuable linear aliphatic compounds.

Language: Английский

Photoinduced Ag-Mediated Azaspirocyclic Approach Involves Cyclization and Dearomatization

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

Published: Nov. 12, 2024

A visible-light-promoted protocol for azaspirocyclic synthesis from

Language: Английский