Construction of Pyrrolidinyl Spirooxindoles via a 1,3-Dipolar Cycloaddition Reaction of (E)-N-Boc-3-Alkylidene-Indolin-2(3H)ones with Azomethine Ylides |
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| Authors: | Zhang-Biao Yu Xiong-Li Liu Bo-Wen Pan Bin Chen Hua-Lin Wang |
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| Affiliation: | 1. Guizhou University , Guiyang , China;2. Traditional Chinese Medicine and Natural Medicine Research and Development Center, College of Life Sciences , Guizhou University , Guiyang , China |
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| Abstract: | A mild and efficient method for the construction of pyrrolidinyl spirooxindoles via a 1,3-dipolar cycloaddition reaction of (E)-N-Boc-3-alkylidene-indolin-2(3H)ones with azomethine ylides has been established. The presence of an N-Boc group in the indolin-2(3H)ones obviously increased the activity and stereoselectivity of the reaction, affording the desired pyrrolidinyl spirooxindoles 4 with up to 85% yield and up to >99/1 dr value. Furthermore, the antibacterial activity of these compounds against Staphylococcus aureus (ATCC-25825) has been tested at minimum concentration, and some of them exhibit moderate antibacterial activity. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications® for the following free supplemental resource(s): Full experimental and spectral details.] |
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| Keywords: | Azomethine ylides cycloaddition reaction spirooxindoles |
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