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

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

References

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14

Crystal data for 4aa: C₁₆H₁₆N₂O₂, M_r = 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) Å^³, Z = 4, T = 296(2) K, ρ_calcd = 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: [phone]; e-mail: [e-mail].