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Org Lett. 2012 Oct 19;14(20):5266-9. doi: 10.1021/ol302425h. Epub 2012 Oct 10.

Synthesis of oxindolyl pyrazolines and 3-amino oxindole building blocks via a nitrile imine [3 + 2] cycloaddition strategy.

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  • 1Sanford-Burnham Medical Research Institute at Lake Nona, 6400 Sanger Road, Orlando, Florida 32827, USA.


The [3 + 2] dipolar cycloaddition reaction of nitrile imines with 3-alkylidene oxindoles is described. The pyrazoline spiroadducts were obtained in high yields and with excellent regio- and diastereoselectivities. These spirocyclic intermediates have been elaborated to synthetically versatile 3-amino oxindole building blocks such as β-amino nitrile, 1,3-diamine, and pyrrolo[2,3-b]indoline derivatives.

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