26447-77-8

Upstream product

• 100-65-2 N-Phenylhydroxylamine 
• 1571-08-0 methyl 4-formylbenzoate 
• 98-95-3 nitrobenzene 

Downstream Products

• 621-06-7 2,N-diphenylacetamide 
• 1402404-07-2 methyl 4-((4S,10aS)-1,1-dimethyl-3-phenyl-3,4,10,10a-tetrahydro-1H-indeno[1,2-e][1,2]oxazepin-4-yl)benzoate 
• 1360631-52-2 3-(4-carbomethoxyphenyl)-2-phenyl-2,3-dihydrobenzo[d]isoxazole 

Relevant academic research and scientific papers

Optimized aqueous Kinugasa reactions for bioorthogonal chemistry applications

Kinugasa reactions hold potential for bioorthogonal chemistry in that the reagents can be biocompatible. Unlike other bioorthogonal reaction products, β-lactams are potentially reactive, which can be useful for synthesizing new biomaterials. A limiting factor for applications consists of slow reaction rates. Herein, we report an optimized aqueous copper(i)-catalyzed alkyne-nitrone cycloaddition involving rearrangement (CuANCR) with rate accelerations made possible by the use of surfactant micelles. We have investigated the factors that accelerate the aqueous CuANCR reaction and demonstrate enhanced modification of a model membrane-associated peptide. We discovered that lipids/surfactants and alkyne structure have a significant impact on the reaction rate, with biological lipids and electron-poor alkynes showing greater reactivity. These new findings have implications for the use of CuANCR for modifying integral membrane proteins as well as live cell labelling and other bioorthogonal applications.

Synthesis of 1,2-Oxazinanes via Hydrogen Bond Mediated [3 + 3] Cycloaddition Reactions of Oxyallyl Cations with Nitrones

Reported herein is the development of [3 + 3] cycloaddition reactions between oxyallyl cations and nitrones to yield 1,2-oxazinane heterocycles. Oxyallyl cation intermediates, generated in situ from α-tosyloxy ketones in the presence of hexafluoro-2-propanol (HFIP), a cosolvent, and a base, are found to react with a range of nitrones to afford 1,2-oxazinanes in good to high yields. The reactions are catalyzed by hydrogen-bond donors such as phenols and squaramides, and dramatically higher diastereoselectivities are observed with 4-nitrophenol.

Studies of multicomponent Kinugasa reactions in aqueous media

Micelle-promoted, copper-catalyzed multicomponent Kinugasa reactions were studied in aqueous media. Reactions were performed in a 'single pot' for a series of in situ generated C,N-diphenylnitrones with Cu(I) phenylacetylide providing β-lactams in yields of 45-85%. Substituents affect the reaction by either accelerating cycloaddition or minimizing side reactions.