10.1002/asia.202100368
Chemistry - An Asian Journal
FULL PAPER
The mixture was stirred under reflux temperature until complete
conversion of propynol to give the intermediate β-amino ketone detected
by TLC analysis. Then halogen source (0.3 mmol) was added to the
reaction system , and the resulted mixture was sequentially stirred under
reflux temperature until the complete conversion of intermediate β-amino
ketone detected by TLC analysis. Finally, the reaction was quenched
with saturated sodium bicarbonate solution, extracted with EtOAc (3×5
mL), washed with saturated brine (3×5 mL), dried over anhydrous
Na2SO4, and concentrated in vacuo to give a residue. The residue was
purified by silica gel with petroleum ether/EtOAc as the elute to afford
products 2, 3, and 4.
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General procedure for the synthesis of 5 and 7
K2CO3 (0.2 mmol) was added to a reaction system of in situ generated
2, 3, and 4 at room temperature, and the resulted mixture was stirred at
room temperature until complete conversation of 2, 3, and 4 detected by
TLC analysis. Finally, the reaction was quenched with saturated sodium
bicarbonate solution, extracted with EtOAc (3×5 mL), washed with
saturated brine (3×5 mL), dried over anhydrous Na2SO4, and
concentrated in vacuo to give a residue. The residue was purified by
silica gel with petroleum ether/EtOAc as the elute to afford acyl aziridines
5.
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Acknowledgements
This work was supported by Science and Technology
Commission of Shanghai Municipality (19DZ2271500) and
Shanghai Municipal Education Commission (Plateau Discipline
Construction Program). Support from Prof. Guanjun Wang was
also greatly appreciated.
Keywords: Meyer-Schuster rearrangement reaction • Acyl
vicinal haloamines • Propargyl alcohols • α-Iodo-β-amino
carbonyl compounds • Aryl aziridinyl ketones
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