Synthesis 2006(20): 3431-3436  
DOI: 10.1055/s-2006-950234
PAPER
© Georg Thieme Verlag Stuttgart · New York

A New Method for the Synthesis of Functionalized 5-Hydroxy-1,5-dihydro-2H-pyrrol-2-one: Reaction of an Enamine, Derived from Addition of a Secondary­ Amine to Dibenzoylacetylene, with an Arylsulfonyl Isocyanate

Abdolali Alizadeh*a, Farnaz Movahedia, Hassan Masrouria, Long-Guan Zhub
a Department of Chemistry, Tarbiat Modarres University, P. O. Box 14115-175, Tehran, Iran
Fax: +98(21)88006544; e-Mail: abdol_alizad@yahoo.com; e-Mail: aalizadeh@modares.ac.ir;
b Chemistry Department, Zhejiang University, Hangzhou 310027, P. R. of China
Further Information

Publication History

Received 22 May 2006
Publication Date:
10 October 2006 (online)

Abstract

An effective route to novel 5-hydroxy-1,5-dihydro-2H-pyrrol-2-one is described which involves the reaction of an en­amine, derived from addition of a secondary amine to dibenzoyl­acetylene, with an arylsulfonyl isocyanate.

    References

  • 1a Bohner B, and Baumann M. inventors; Swiss Patent  633678.  ; Chem. Abstr. 1983, 98, 121386
  • 1b Bohner B, and Baumann M. inventors; Ger. Patent  2735841.  ; Chem. Abstr. 1983, 88, 152415
  • 2 James GD. Mills S. Pattenden G. J. Chem. Soc., Perkin Trans. 1  1993,  2581 
  • 3a Jimenez MD. Ortega R. Tito A. Farina F. Heterocycles  1988,  27:  173 
  • 3b Irgolic KJ. In Houben-Weyl   Vol. E12b, 4th ed.:  Klamann D. Thieme; Stuttgart: 1990.  p.150 
  • 4 Gossauer A. Tetrahedron  1983,  39:  1933 
  • 5 Wiedhopf RM. Trumbull ER. Cole JR. J. Pharm. Sci.  1973,  62:  1206 
  • 6 Kuckländer U. Enamines as Synthones, In The Chemistry of Enamines   Rappoport Z. Wiley; New York: 1994.  p.523 
  • 7 Michael JP. de Konig CB. Gravestock D. Hosken GD. Howard AS. Jungmann CM. Krause RWM. Parsons AS. Pelly SC. Stanbury TV. Pure Appl. Chem.  1999,  71:  979 
  • 8 Lyutenko NV. Gerus II. Kacharov AD. Kukhar VP. Tetrahedron  2003,  59:  1731 
  • 9 Gerus II. Lyutenko NV. Kacharov AD. Kukhar VP. Tetrahedron Lett.  2000,  41:  10141 
  • 10 Gao Y. Shirai M. Sato F. Tetrahedron Lett.  1997,  38:  6849 
  • 11 Skattebol L. Jones ERH. Whiting MC. Org. Synth., Coll. Vol. IV   Wiley; New York: 1963.  p.792 
  • 12 Bowden K. Heilbron IM. Jones ERH. Weedon BC. J. Chem. Soc.  1946,  39