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Synthesis 2013; 45(15): 2165-2170
DOI: 10.1055/s-0033-1339180
paper
© Georg Thieme Verlag Stuttgart · New York

Novel Role of p-Toluenesulfonamide in the Preparation of 4,5-Diaminocyclopent-2-enones

Jinqian Liu
Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, P. R. of China   Fax: +86(21)64253881   Email: wanglimin@ecust.edu.cn   Email: jjYu@ecust.edu.cn
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Jianjun Yu*
Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, P. R. of China   Fax: +86(21)64253881   Email: wanglimin@ecust.edu.cn   Email: jjYu@ecust.edu.cn
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Mengyun Zhu
Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, P. R. of China   Fax: +86(21)64253881   Email: wanglimin@ecust.edu.cn   Email: jjYu@ecust.edu.cn
,
Jun Li
Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, P. R. of China   Fax: +86(21)64253881   Email: wanglimin@ecust.edu.cn   Email: jjYu@ecust.edu.cn
,
Xingzhou Zheng
Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, P. R. of China   Fax: +86(21)64253881   Email: wanglimin@ecust.edu.cn   Email: jjYu@ecust.edu.cn
,
Limin Wang*
Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, P. R. of China   Fax: +86(21)64253881   Email: wanglimin@ecust.edu.cn   Email: jjYu@ecust.edu.cn
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Publication History

Received: 04 March 2013

Accepted after revision: 07 May 2013

Publication Date:
12 June 2013 (online)

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Abstract

A new and efficient protocol for the preparation of 4,5-diaminocyclopent-2-enones via the reaction of N-sulfonylimine with secondary amines, with p-toluenesulfonamide acting as a leaving group, is presented. In addition, p-toluenesulfonamide worked well as a catalyst even with a catalytic amount for the reaction of 2-furaldehyde and secondary amines to afford the corresponding products in higher yields.

Key words

TsNH2 - p-toluenesulfonamide - leaving group - catalyst - secondary amines - 4,5-diaminocyclopent-2-enones

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