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
,
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
› Author Affiliations
Further Information

Publication History

Received: 04 March 2013

Accepted after revision: 07 May 2013

Publication Date:
12 June 2013 (online)


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

 
  • References

    • 1a Piancatelli G, Dauria M, Donofrio F. Synthesis 1994; 867
    • 1b Arjona O, Gomez AM, Lopez JC, Plumet J. Chem. Rev. 2007; 107: 1919
    • 2a Davis FA, Deng J. Org. Lett. 2005; 7: 621
    • 2b Domostoj MM, Irving E, Scheinmann F, Hale KJ. Org. Lett. 2004; 6: 2615 ; and references cited therein
    • 3a Lewis KG, Mulquiney CE. Tetrahedron 1977; 33: 463
    • 3b McGowan JC. J. Chem. Soc. 1949; 777
    • 3c McGowan JC. J. Chem. Soc. 1954; 4032
    • 3d Lewis KG, Mulquiney CE. Aust. J. Chem. 1979; 32: 1079
    • 3e Hofmann T. J. Agric. Food Chem. 1998; 46: 932
  • 4 Li SW, Batey RA. Chem. Commun. 2007; 3759
  • 5 Ramesh D, Srikanth RT, Narasimhulu M, Rajaram S, Suryakiran N, Chinni MK, Venkateswarlu Y. Chem. Lett. 2009; 38: 586
    • 6a Seong MR, Lee HJ, Kim JN. Tetrahedron Lett. 1998; 39: 6219
    • 6b Enders D, Narine AA, Toulgoat F, Bisschops T. Angew. Chem. Int. Ed. 2008; 47: 5661
    • 6c Li H.-H, Dong D.-J, Tian S.-K. Eur. J. Org. Chem. 2008; 3623
    • 6d Liu C.-R, Li M.-B, Cheng D.-J, Yang C.-F, Tian S.-K. Org. Lett. 2009; 11: 2543
    • 6e He Q.-L, Sun F.-L, Zheng X.-J, You S.-L. Synlett 2009; 1111
    • 6f Sun F.-L, Zheng X.-J, Gu Q, He Q.-L, You S.-L. Eur. J. Org. Chem. 2010; 47
    • 6g Esquivias J, Carretero JC. Angew. Chem. Int. Ed. 2006; 45: 629
    • 6h Alonso I, Esquivias J, Carretero JC. J. Org. Chem. 2008; 73: 6401
    • 6i Liu C.-R, Li M.-B, Yang C.-F, Tian S.-K. Chem. Commun. 2008; 1249
    • 6j Liu C-R, Li M-B, Yang C-F, Tian S-K. Chem. Eur. J. 2009; 15: 793
  • 7 Stenhouse J. Justus Liebigs Ann. Chem. 1850; 74: 278
    • 8a Becher J. Synthesis 1980; 589
    • 8b Chengand WC, Kurth MJ. Org. Prep. Proced. Int. 2002; 34: 585
  • 9 Liu J.-Q, Wang L.-M, Zheng X.-Z, Wang A.-L, Zhu M.-Y, Yu J.-J, Sheng Q. Tetrahedron Lett. 2012; 53: 1843
  • 10 See Supporting Information for details.