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Pd-Catalyzed cycloisomerization/nucleophilic addition/reduction: an efficient method for the synthesis of spiro-pseudoindoxyls containing N,N′-ketal

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Abstract

An efficient method for the synthesis of C2-spiropseudoindoxyls which are common structural units prevalent in indole alkaloids was developed. A study of the mechanism indicated that this protocol involved a Pd-catalyzed 5-exo-dig nitroalkyne cyclization and an internal N–O bond redox process. The fungicidal activity evaluation of representative compounds highlighted this reaction for the construction of bioactive functionalized spiro-heterocycles.

Graphical abstract: Pd-Catalyzed cycloisomerization/nucleophilic addition/reduction: an efficient method for the synthesis of spiro-pseudoindoxyls containing N,N′-ketal

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Publication details

The article was received on 07 Apr 2017, accepted on 21 May 2017 and first published on 23 May 2017


Article type: Research Article
DOI: 10.1039/C7QO00272F
Citation: Org. Chem. Front., 2017, Advance Article
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    Pd-Catalyzed cycloisomerization/nucleophilic addition/reduction: an efficient method for the synthesis of spiro-pseudoindoxyls containing N,N′-ketal

    L. Chen, J. Xie, H. Song, Y. Liu, Y. Gu and Q. Wang, Org. Chem. Front., 2017, Advance Article , DOI: 10.1039/C7QO00272F

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