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Direct construction of 3',4'-dihydrospiro[pyrrol-3,2'-oxindoles] through a cascade Michael/cyclization reaction of 3-aminoindolin-2-ones with enones/enals

Dao-Cai Wang ,  Hang Song ,  Chun-Yun Xu ,  Hui Dong ,  Jie Liu

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Citation:  Dao-Cai Wang, Hang Song, Chun-Yun Xu, Hui Dong, Jie Liu. Direct construction of 3',4'-dihydrospiro[pyrrol-3,2'-oxindoles] through a cascade Michael/cyclization reaction of 3-aminoindolin-2-ones with enones/enals[J]. Chinese Chemical Letters, 2015, 26(8): 1050-1053. doi: 10.1016/j.cclet.2015.04.014 shu

Direct construction of 3',4'-dihydrospiro[pyrrol-3,2'-oxindoles] through a cascade Michael/cyclization reaction of 3-aminoindolin-2-ones with enones/enals

    • 通讯作者: Jie Liu,
  • 基金项目:

    Financial support for this work by the National Natural Science Foundation of China (No. 81202403)  (No. 81202403)

    Technology Department Translational Medicine Innovation Foundation (No. ZH13039) are gratefully acknowledged. We also thank Sichuan University Analytical & Testing Center for the NMR analysis. (No. ZH13039)

摘要: A simple and efficient cascade Michael/cyclization reaction of 3-aminoindolin-2-ones with enones/enals was identified for the synthesis of potentially biologically active 3',4'-dihydrospiro[pyrrol-3,2'-oxindoles], using DBU as an efficient catalyst and ethylene glycol as an environmentally benign solvent. More diverse 3',4'-dihydrospiro[pyrrol-3,2'-oxindoles] analog libraries were prepared in good yields (up to 97%). The structure of 3',4'-dihydrospiro[pyrrol-3,2'-oxindoles] was confirmed by mass spectrometry analysis, NMR analysis and single crystal X-ray diffraction. The main advantages of this method include the availability of startingmaterials, simple experimental operation, short reaction time, as well as high yields observed.

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  • 发布日期:  2015-04-19
  • 收稿日期:  2015-01-20
  • 网络出版日期:  2015-04-03
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