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

Cheng Zhang; Shanliang Dong; Yang Zheng; Ciwang He; Jiaolong Chen; Jingsen Zhen; Lihua Qiu; Xinfang Xu

doi:10.1039/C7OB02802D

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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†

Cheng Zhang,^a Shanliang Dong,^a Yang Zheng,^a Ciwang He,^a Jiaolong Chen,^a Jingsen Zhen,^a Lihua Qiu*^a and Xinfang Xu

*^a

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* Corresponding authors

^a Key Laboratory of Organic Synthesis of Jiangsu Province; College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, P. R. China
E-mail: qiulihua@suda.edu.cn, xinfangxu@suda.edu.cn

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.

This article is part of the themed collection: Synthetic methodology in OBC

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DOI: https://doi.org/10.1039/C7OB02802D
Article type: Communication
Submitted: 16 Nov 2017
Accepted: 05 Dec 2017
First published: 06 Dec 2017

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Org. Biomol. Chem., 2018,16, 688-692

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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, 16, 688 DOI: 10.1039/C7OB02802D

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Organic & Biomolecular Chemistry

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

Abstract

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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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