Synthesis of Functionalized 3-Spiro[cyclopropa[a]pyrrolizine]- and 3-Spiro[3-azabicyclo[3.1.0]hexane]oxindoles from Cyclopropenes and Azomethine Ylides via [3+2]-Cycloaddition
Synthesis of Functionalized 3-Spiro[cyclopropa[a]pyrrolizine]- and 3-Spiro[3-azabicyclo[3.1.0]hexane]oxindoles from Cyclopropenes and Azomethine Ylides via [3+2]-Cycloaddition
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DOI：
10.1021/acs.joc.6b02505
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发表时间：
2017-01-20
影响因子：
3.6
通讯作者：
Stepakov, Alexander V.
中科院分区：
文献类型：
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作者：
Filatov, Alexander S.;Knyazev, Nickolay A.;Stepakov, Alexander V.
3-螺环[a]吡咯烷]和3-螺环[3-氮杂双环[3.1.0]己烷]氧吲哚是以取代的板蓝素、α-氨基酸和环丙烯为原料，通过一锅三组分反应，以中高的产率合成的。关键步骤是原位生成的亚甲基叶立德与环丙烯的分子内[3+2]-环加成反应。N-取代和N-未取代的α-氨基酸、甘氨酸二肽和苯甲胺都被用作生成亚甲基叶立德的胺组分。用流式细胞仪检测了部分化合物对人白血病K562细胞株的体外抗肿瘤活性。
3-Spiro[cyclopropa[a]pyrrolizine]- and 3-spiro[3-azabicyclo[3.1.0]hexane]oxindoles were prepared in moderate to high yields via one-pot three-component reactions using substituted isatins, alpha-amino acids, and cyclopropenes. The key step is an intramolecular [3 + 2]-cycloaddition reaction of an in situ generated azomethine ylide onto a cyclopropene. Both N-substituted and N-unsubstituted alpha-amino acids, dipeptide Gly-Gly, and also benzylamine were used as the amine component for the azomethine ylide generation. The anticancer activity of some of the obtained compounds against human leukemia K562 cell line was evaluated by flow cytometry in vitro.