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

Autoren

  • 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
  • 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
  • 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
Weitere Informationen

Publikationsverlauf

Received: 04. März 2013

Accepted after revision: 07. Mai 2013

Publikationsdatum:
12. Juni 2013 (online)


Graphical Abstract

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.

Supporting Information