Regioselective [3 + 2]-annulation of hydrazonyl chlorides with 1,3-dicarbonyl compounds for assembling of polysubstituted pyrazoles

Kun Liu; Xinye Shang; Yuyu Cheng; Xiaoyong Chang; Pengfei Li; Wenjun Li

doi:10.1039/C8OB02352B

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Regioselective [3 + 2]-annulation of hydrazonyl chlorides with 1,3-dicarbonyl compounds for assembling of polysubstituted pyrazoles†

Kun Liu,^a Xinye Shang,^a Yuyu Cheng,^b Xiaoyong Chang,^b Pengfei Li*^b and Wenjun Li

*^a

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* Corresponding authors

^a Department of Medicinal Chemistry, School of Pharmacy, Qingdao University, Qingdao, Shandong, China
E-mail: liwj@qdu.edu.cn

^b Department of Chemistry and Shenzhen Grubbs Institute, Southern University of Science and Technology, Shenzhen, Guangdong, China
E-mail: lipf@sustc.edu.cn, flyli1980@gmail.com

Abstract

A facile approach to polysubstituted pyrazoles from hydrazonyl chlorides and 1,3-dicarbonyl compounds has been developed. In the presence of DMAP combined with Et₃N, hydrazonyl chlorides reacted with N-phenyl-3-oxobutanamides smoothly to afford a series of polysubstituted pyrazoles in 67–98% yields via the [3 + 2]-cycloaddition.

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

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DOI: https://doi.org/10.1039/C8OB02352B
Article type: Communication
Submitted: 21 Sep 2018
Accepted: 11 Oct 2018
First published: 11 Oct 2018

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Org. Biomol. Chem., 2018,16, 7811-7814

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Regioselective [3 + 2]-annulation of hydrazonyl chlorides with 1,3-dicarbonyl compounds for assembling of polysubstituted pyrazoles

K. Liu, X. Shang, Y. Cheng, X. Chang, P. Li and W. Li, Org. Biomol. Chem., 2018, 16, 7811 DOI: 10.1039/C8OB02352B

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Organic & Biomolecular Chemistry

Regioselective [3 + 2]-annulation of hydrazonyl chlorides with 1,3-dicarbonyl compounds for assembling of polysubstituted pyrazoles†

Abstract

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Regioselective [3 + 2]-annulation of hydrazonyl chlorides with 1,3-dicarbonyl compounds for assembling of polysubstituted pyrazoles

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