期刊
RSC ADVANCES
卷 10, 期 24, 页码 14122-14133出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/d0ra02374d
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资金
- Russian Foundation for Basic Research [19-03-00201, 19-33-90282]
- M. V. Lomonosov Moscow State University Program of Development
A new synthetic approach for realizing biologically relevant bis-aryl spiro[azetidine-2,3 '-indoline]-2 ',4-diones was developed based on Staudinger ketene-imine cycloaddition through the one-pot reaction of substituted acetic acids and Schiff bases in the presence of oxalyl chloride and an organic base. A series of [azetidine-2,3 '-indoline]-2 ',4-diones were synthesized using this method. For comparison, the same compounds were obtained using a known technique, where ketene is generated from pre-synthesized acyl chloride. It was shown that the use of oxalyl chloride for ketene generation in the one-pot reaction at room temperature allows for the reversal of the diastereoselectivity of spiro-lactam formation, unlike previously described procedures.
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