A new highly convergent entry to densely functionalized aziridines based on the Ugi reaction

被引:12
作者
Banfi, Luca [1 ]
Basso, Andrea [1 ]
Guanti, Giuseppe [1 ]
Paravidino, Monica [1 ]
Riva, Renata [1 ]
机构
[1] Dipartimento Chim & Chim Ind, I-16146 Genoa, Italy
来源
QSAR & COMBINATORIAL SCIENCE | 2006年 / 25卷 / 5-6期
关键词
multicomponent reactions; Ugi four-component reaction (U-4CR); isocyanide; aziridines; post-condensation transformations;
D O I
10.1002/qsar.200540192
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
The products of an Ugi-4CR employing lactate-derived O-protected alpha-hydroxycarbonyl derivatives underwent, during the subsequent O-deprotection reaction, an unexpected acyl migration from nitrogen to oxygen. After ester saponification, treatment of the resulting alpha-aminoalcohol with mesyl chloride gave rise to a regioselective and stereospecific cyclization to give a series of highly functionalized aziridines in good overall yield.
引用
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页码:457 / 460
页数:4
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