Efficient synthesis of 1,2-bis(alkoxycarbonyl)pyrazol-3-ones from 2,3-allenoic acids, azodicarboxylates and PPh3

Ruizhi Lü; Xin Cheng; Xingliang Zheng; Shengming Ma

doi:10.1039/C3CC48215D

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Efficient synthesis of 1,2-bis(alkoxycarbonyl)pyrazol-3-ones from 2,3-allenoic acids, azodicarboxylates and PPh₃†

Ruizhi Lü,^a Xin Cheng,^b Xingliang Zheng^bc and Shengming Ma*^ab

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* Corresponding authors

^a Shanghai Key Laboratory of Green Chemistry and Chemical Process, Department of Chemistry, East China Normal University, 3663 North Zhongshan Lu, Shanghai 200062, Peoples Republic of China
E-mail: masm@sioc.ac.cn
Fax: +86-21-6260-9305

^b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Fenglin Lu, Shanghai 200032, P. R. China

^c College of Chemistry and Biologic Engineering, Changsha University of Science & Technology, 96 Wajiali Lu, Changsha 414044, P. R. China

Abstract

An efficient cascade reaction of 2,3-allenoic acids with dialkyl azodicarboxylate in the presence of PPh₃ affording 1,2-bis(alkoxycarbonyl)pyrazol-3-ones in moderate yields has been developed. The reaction may proceed via the intramolecular Michael addition of the expected 2,3-allenoyl hydrazines.

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Article information

DOI: https://doi.org/10.1039/C3CC48215D
Article type: Communication
Submitted: 27 Oct 2013
Accepted: 30 Nov 2013
First published: 02 Dec 2013

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Chem. Commun., 2014,50, 1537-1539

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Efficient synthesis of 1,2-bis(alkoxycarbonyl)pyrazol-3-ones from 2,3-allenoic acids, azodicarboxylates and PPh₃

R. Lü, X. Cheng, X. Zheng and S. Ma, Chem. Commun., 2014, 50, 1537 DOI: 10.1039/C3CC48215D

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