Synthesis 2008(20): 3223-3228  
DOI: 10.1055/s-0028-1083159
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Facile and Highly Regiospecific Synthesis of 2-Aryl-Substituted Pyrazolidin-3-ones from α,β-Unsaturated N-Acylbenzotriazoles and Arylhydrazines

Xiaoxia Wang*a, Wencun Wanga, Yihang Wena, Liang Hea, Xiangming Zhub
a Zhejiang Key Laboratory for Reactive Chemistry on Solid Surfaces, College of Chemistry and Life Sciences, Zhejiang Normal University, Jinhua 321004, P. R. China
Fax: +86(579)82282595; e-Mail: wangxiaoxia@zjnu.cn;
b UCD School of Chemistry and Chemical Biology, University College Dublin, Belfield, Dublin 4, Ireland
Further Information

Publication History

Received 4 June 2008
Publication Date:
25 September 2008 (online)

Abstract

The bis-addition of arylhydrazines to α,β-unsaturated N-acylbenzotriazoles to form heterocyclic compounds was achieved in refluxing THF by using triethylamine as promoter. The reaction was highly regioselective and various 2-aryl-substituted pyrazolidin-3-ones were obtained in moderate to good yields.

    References

  • 1a Chen W. Yuan XH. Li R. Du W. Wu Y. Ding LS. Chen YC. Adv. Synth. Catal.  2006,  348:  1818 
  • 1b Pezdirc L. Groselj U. Meden A. Stanovnik B. Svete J. Tetrahedron Lett.  2007,  48:  5205 ; and references cited therein
  • 1c Couloigner E. Cartier D. Labia R. Bioorg. Med. Chem. Lett.  1999,  9:  2205 
  • 1d Blanchard WB, Britton TC, and Varie DL. inventors; US Patent  5399708.  ; Chem. Abstr. 1995, 123, 228177
  • 1e Holmes RE. Neel DA. Tetrahedron Lett.  1990,  31:  5567 
  • 1f Jungheim LN. Sigmund SK. J. Org. Chem.  1987,  52:  4007 
  • 1g Indelicato JM. Pasini CE. J. Med. Chem.  1988,  31:  1227 
  • 1h Long WE, Tirel MD, Gent MH, and Webb TC. inventors; US Patent  4753869.  ; Chem. Abstr. 1988, 105, 143486
  • 1i Ernest FG. inventors; US Patent  3178441.  ; Chem. Abstr. 1965, 63, 39145
  • 2a Perri ST. Slater SG. Toske SG. White JD. J. Org. Chem.  1990,  55:  6037 
  • 2b Shi H. Zhu HJ. Wang JT. Acta Crystallogr., Sect. E: Struct. Rep. Online  2006,  62:  233 
  • 2c Shi H. Zhu HJ. Yin PW. Wang JT. Shi XL. Acta Crystallogr., Sect. E: Struct. Rep. Online  2005,  61:  2246 
  • 2d Marton GL. Marton AL. Rev. Chim. (Bucharest, Rom.)  2004,  55:  555 ; Chem. Abstr. 2004, 142, 197957
  • 2e Marton AL. Marton GI. Rev. Chim. (Bucharest, Rom.)  2002,  53:  51 ; Chem. Abstr. 2002, 137, 125117
  • 2f Taniguchi M, and Yamakawa K. inventors; Japanese Patent  11060559.  ; Chem. Abstr. 1997, 130, 223270
  • 3 Sibi MP. Soeta T. J. Am. Chem. Soc.  2007,  129:  4522 
  • 4 Kim KS. Ryan PC. Heterocycles  1990,  31:  79 
  • 5 Katritzky AR. Suzuki K. Wang Z. Synlett  2005,  1656 
  • 6 Katritzky AR. Wang M. Zhang S. Arkivoc  2001,  (ix):  19 
  • 7 Katritzky AR. Cai C. Singh SK. J. Org. Chem.  2006,  71:  3375 
  • 8 Wang XX. Zou XF. Du JX. J. Chem. Res., Synop.  2006,  64 
  • 9 Katritzky AR. Meher NK. Singh SK. J. Org. Chem.  2005,  70:  7792 
  • 10 Katritzky AR. Le KNB. Khelashvili L. Mohapatra PP. J. Org. Chem.  2006,  71:  9861 
  • 11 Zou XF. Wang XX. Cheng CG. Kong LC. Mao H. Tetrahedron Lett.  2006,  47:  3767 
  • 12 Wang XX. Yu HP. Xu PF. Zheng RW. J. Chem. Res., Synop.  2005,  595 
  • 13a Diab J. Laurent A. Drean IL. J. Fluorine Chem.  1997,  84:  145 
  • 13b Touzot A. Soufyane M. Berber H. Toupet L. Mirand C. J. Fluorine Chem.  2004,  125:  1299 
  • 15a Bishiop BC. Brands KMJ. Gibb AD. Kennedy DJ. Synthesis  2004,  43 
  • 15b Xie F. Cheng G. Hu YH. J. Comb. Chem.  2006,  8:  286 
  • 16 Katritzky AR. Zhang Y. Singh SK. Synthesis  2003,  2795 
14

Crystal data for 4aa: C16H16N2O2, Mr = 268.31, colorless crystal (0.41 × 0.15 × 0.05 mm), monoclinic, space group P21/c, a = 8.6609(4) Å, b = 6.0272(3) Å, c = 27.1719(13) Å, β = 105.494(4)˚, V = 1366.85(11) ų, Z = 4, T = 296(2) K, ρcalcd = 1.304 g˙cm, F(000) = 568, µ = 0.087 mm, R1 = 0.0594, wR2 = 0.1527 and S = 1.048 for 1810 reflections with I > 2σ(I). The structure was solved by direction methods and difference Fourier syntheses. Nonhydrogen atoms were refined anisotropically, and all hydrogen atoms were placed at ideal positions and allowed to ride. The crystallographic calculations were conducted using the SHELXL-97 programs. Detail crystallographic data of 4aa have been deposited at Cambridge Crystallographic Data Center under CCDC-687432. These data can be obtained free of charge from www.ccdc.cam.ac.uk/conts/retrieving.html [or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK; fax: +44 1223 336 033; e-mail: deposit@ccdc.cam.ac.uk.