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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
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Publication History

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

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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.

Key words

bis-addition - regioselectivity - arylhydrazine - α,β-unsaturated N-acylbenzotriazole - pyrazolidinone

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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-³, F(000) = 568, µ = 0.087 mm-¹, 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.