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Synthesis of spiro-4H-pyrazole-oxindoles and fused 1H-pyrazoles via divergent, thermally induced tandem cyclization/migration of alkyne-tethered diazo compounds

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Abstract

A thermally induced, substrate-dependent reaction of alkynyl diazo compounds has been developed. This transformation produces spiro-4H-pyrazole-oxindoles and fused 1H-pyrazoles in good to high yields from the corresponding alpha-cyano and alpha-sulfonyl diazo compounds. The salient features of this reaction include excellent chemoselectivity and atom-economy, mild reaction conditions, simple purification and potential for large scale production.

Graphical abstract: Synthesis of spiro-4H-pyrazole-oxindoles and fused 1H-pyrazoles via divergent, thermally induced tandem cyclization/migration of alkyne-tethered diazo compounds

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Publication details

The article was received on 16 Nov 2017, accepted on 05 Dec 2017 and first published on 06 Dec 2017


Article type: Communication
DOI: 10.1039/C7OB02802D
Citation: Org. Biomol. Chem., 2018, Advance Article
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    Synthesis of spiro-4H-pyrazole-oxindoles and fused 1H-pyrazoles via divergent, thermally induced tandem cyclization/migration of alkyne-tethered diazo compounds

    C. Zhang, S. Dong, Y. Zheng, C. He, J. Chen, J. Zhen, L. Qiu and X. Xu, Org. Biomol. Chem., 2018, Advance Article , DOI: 10.1039/C7OB02802D

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