Synthesis of Some New Chiral Triazole-oxazoline Derivatives

Current Organic Synthesis, Journal Year: 2024, Volume and Issue: 22(1), P. 136 - 142

Published: July 12, 2024

: Some new (S)-2-[1-aryl-5-methyl-1H-1,2,3-triazol-4-yl]-4-benzyl-4,5-dihydro-ox-azoline were synthesized by the reaction of (S)-N-(1-hydroxy-3-phenylpropan-2-yl)-1-aryl-5-methyl-1H-1,2,3-triazole-4-carboxamides which prepared from aromatic amine as start-ing materials, with p-toluenesulfonyl chloride, triethylamine and DMAP. The structures characterized 1H NMR, 13C MS IR. chiral triazole-oxazoline was used a ligand in Diels-Alder asymmetric catalytic between 3-allyl-1,3-ox-azolidin-2-ketone 2-methyl-1,3-butadiene, using PdCl2 catalyst. (S)-3-(4-methylcyclo-hexe-3-ene-1-formyl)-1,3-oxazolidin-2-one obtained. Background: ligands are rarely reported. Objective: aim study to synthsize some (S)-4-benzyl-2-(1-aryl-5-methyl-1H-1,2,3-triazole-4-yl)-4,5-dihydrooxazoline (5a-g). Methods: one-pot methods oriented synthesis adopted. This provides sim-ple effective method for derivatives. Results: (5a-g) cyclization 3-allyl-1,3-oxazolidin-2-ketone 2-methyl-1,3-butadiene catalyzed (S)-4-triazole-oxazoline ligands. Conclusion: (S)-4-benzyl-2-(1-aryl-5-methyl-1H-1,2,3-triazole-4-yl)-4,5-dihydro-oxazoline corresponding N-[(S)-1-hydroxy-3-phenylpropan-2-yl]-1-aryl-5-methyl-1H-1,2,3-triazole-4-formamide, through method. After preliminary evaluation, triazoline-oxazoline ligands, 1,2,3-triazole rings, like pyridine-type materials saved replace one oxazoline ring di-oxazoline reactions.

Language: Английский

Investigations on the Synthesis of Chiral Ionic-Liquid-Supported Ligands and Corresponding Transition-Metal Catalysts: Strategy and Experimental Schemes

Molecules, Journal Year: 2024, Volume and Issue: 29(23), P. 5661 - 5661

Published: Nov. 29, 2024

Ionic liquids have been utilized in numerous significant applications within the field of chemistry, particularly organic due to their unique physical and chemical properties. In realm asymmetric transition-metal-catalyzed transformations, chiral ionic-liquid-supported ligands corresponding transition-metal complexes facilitated these processes unconventional solvents, especially ionic water. These innovative reaction systems enable recycling catalysts while producing optically active molecules with comparable or even higher levels chemo-, regio-, stereoselectivity compared parent catalysts. this short review, we aim provide an overview structures synthetic pathways for Various methodologies are demonstrated based on conceptual frameworks diverse ligands. We systematically present comprehensive typical that readily applied processes, categorized by ligand framework. Notably, crucial experimental procedures delineated exhaustive detail, objective enhancing comprehension pivotal aspects involved constructing ionic-liquid-tagged compounds both scholars readers. Considering current limitations such catalysts, conclude remarks several potential research directions future breakthroughs synthesis application intriguing

Language: Английский