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Synlett 2013; 24(19): 2591-2595
DOI: 10.1055/s-0033-1339642
letter
© Georg Thieme Verlag Stuttgart · New York

A Diastereoselective Synthesis of Functionalized 3-Pyrazolidinones from ­Hydrazines, Aromatic Aldehydes, and Acylketene

Issa Yavari*
a   Department of Chemistry, Tarbiat Modares University, PO Box 14115-175, Tehran, Iran   Fax: +98(21)82883455   Email: yavarisa@modares.ac.ir
,
Mohammad J. Bayat
a   Department of Chemistry, Tarbiat Modares University, PO Box 14115-175, Tehran, Iran   Fax: +98(21)82883455   Email: yavarisa@modares.ac.ir
,
Stavroula Skoulika
b   Laboratory of Physical Chemistry, Department of Chemistry, The University of Ioannina, 45110 Ioannina, Greece
› Author Affiliations
Further Information

Publication History

Received: 15 July 2013

Accepted after revision: 21 July 2013

Publication Date:
18 September 2013 (online)

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Abstract

A practical microwave-assisted, one-pot method for the construction of 4-acetyl-2-phenyl-5-aryl-3-pyrazolidinones via a tandem reaction between phenylhydrazine, aromatic aldehydes, and but-1-ene-1,3-dione (acylketene), in moderate to good yields, is reported. When methylhydrazine and 4-methylphenylhydrazine ­hydrochloride were used instead of phenylhydrazine, the reaction led to the formation of 3-oxobutanohydrazide derivatives.

Key words

hydrazines - aromatic aldehydes - 1,3-dioxinone - microwave irradiation - acylketene
 

  • References and Notes

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  • 30 General Procedure for the Synthesis of Compounds 4 and 6A solution of aryl(alkyl)hydrazine (1 mmol) and aldehydes 2 (1.2 mmol) was stirred in toluene (5 mL) for 10 min. Then, 3 (0.19 g, 1.3 mmol) was added, irradiated under microwave at 900 W. After completion of the reaction [about 1 h; TLC monitoring (EtOAc–hexane, 1: 5)], the solvent was evaporated, and the residue was purified by column chromatography [silica gel (230–400 mesh; Merck), EtOAc–hexane, 1:5] to give pure product.4-Acetyl-2,5-diphenylpyrazolidin-3-one (4a)Yellow powder; mp 124–126 °C; yield: 0.23 g (83%). IR (KBr): 3384, 3051, 2923, 1691, 1618, 1500, 1457 cm–1. 1H NMR (500.1 MHz, CDCl3): δ = 2.51 (3 H, s, Me), 3.96 (1 H, d, 3 J = 4.4 Hz, CH), 5.17 (1 H, d, 3 J = 4.4 Hz, CH), 5.35 (1 H, br s, NH), 7.18 (1 H, d, 3 J = 7.4 Hz, CH), 7.33–7.37 (2 H, m, CH), 7.39 (2 H, t, 3 J = 8.0 Hz, CH), 7.48 (2 H, d, 3 J = 7.9 Hz, CH), 7.58 (1 H, m, CH),7.92 (2 H, d, 3 J = 7.8 Hz, CH) ppm. 13C NMR (125.7 MHz, CDCl3): δ = 29.7 (Me), 58.2 (CH), 66.2 (CH), 124.9 (2 CH), 125.9 (2 CH), 126.8 (C), 128.1 (CH), 128.5 (CH), 128.9 (2 CH), 129.0 (2 CH), 132.9 (C), 138.9 (C), 165.5 (C), 201.7 (C) ppm. MS (EI): m/z (%) = 280 (24) [M+], 278 (80), 263 (59), 91 (25), 77 (52). Anal. Calcd for C17H16N2O2 (280.32): C, 72.84; H, 5.75; N, 9.99. Found: C, 72.39; H, 5.84; N, 10.08.4-Acetyl-2-phenyl-5-p-tolylpyrazolidin-3-one (4b)Yellow powder; mp 123–125 °C; yield: 0.24 g (82%). IR (KBr): 3395, 3032, 2919, 1685, 1619, 1505 cm–1. 1H NMR (500.1 MHz, CDCl3): δ = 2.34 (3 H, s, Me), 2.50 (3 H, s, Me), 3.96 (1 H, d, 3 J = 4.6 Hz, CH), 5.12 (1 H, d, 3 J = 4.6 Hz, CH), 5.23 (1 H, br s, NH), 7.16–7.19 (3 H, m, CH), 7.24 (2 H, d, 3 J = 8.0 Hz, CH), 7.38 (2 H, d, 3 J = 7.7 Hz, CH), 7.91 (2 H, d, 3 J = 8.0 Hz, CH) ppm. 13C NMR (125.7 MHz, CDCl3): δ = 21.1 (Me), 29.7 (Me), 58.2 (CH), 66.0 (CH), 118.8 (2 CH), 120.9 (C), 124.6 (CH), 126.1 (2 CH), 128.9 (2 CH), 129.8 (2 CH), 138.0 (C), 138.4 (C), 165.7 (C), 201.8 (C) ppm. MS (EI): m/z (%) = 294 (14) [M+], 292 (80), 277 (58), 91 (43), 77 (24). Anal. Calcd for C18H18N2O2 (294.35): C, 73.45; H, 6.16; N, 9.52. Found: C, 73.78; H, 6.07; N, 9.57.4-Acetyl-5-(2-chlorophenyl)-2-phenylpyrazolidin-3-one (4c)Yellow powder; mp 113–115 °C; yield: 0.27 g (85%). IR (KBr): 3424, 3059, 2924, 1698, 1625, 1554, 1497 cm–1. 1H NMR (500.1 MHz, CDCl3): δ = 2.53 (3 H, s, Me), 3.85 (1 H, d, 3 J = 3.2 Hz, CH), 5.30 (1 H, d, 3 J = 3.2 Hz, CH), 5.38 (1 H, br s, NH), 7.19–7.25 (3 H, m, CH), 7.38 (2 H, d, 3 J = 6.5 Hz, CH), 7.42–7.47 (2 H, m, CH), 8.01 (2 H, d, 3 J = 7.9 Hz, CH) ppm. 13C NMR (125.7 MHz, CDCl3): δ = 31.9 (Me), 56.0 (CH), 66.3 (CH), 118.1 (2 CH), 124.9 (CH), 127.0 (CH), 127.4 (CH), 129.0 (2 CH), 129.1 (CH), 129.8 (CH), 131.8 (C), 137.3 (C), 138.2 (C), 165.0 (C), 201.8 (C) ppm. MS (EI): m/z (%) = 314 (15) [M+], 312 (55), 297 (35), 91 (15), 77 (63). Anal. Calcd for C17H15ClN2O2 (314.77): C, 64.87; H, 4.80; N, 8.90. Found: C, 65.15; H, 4.74; N, 9.01.X-ray Crystal-Structure Determination of 4c – Structure-Determination and Refinement DataFormula: C17H15ClN2O2; M r 314.76; triclinic, space group: P1, a = 9.863(1), b = 10.850(1), c = 15.029(2) Å, α = 94.69(1)°, δ = 90.35(1)°, γ = 96.32(1)°; Z = 2, V = 1593.0(3) Å3, D calcd = 1.312 mg/m3; Mo-Kα radiation (0.71073 Å); T = 293(2) K. 6580 reflections collected on a Bruker P4 diffractometer, 5545 unique (R int = 0.0284). All heavy atoms have been located by difference Fourier maps and refined anisotropically. All hydrogen atoms except that of the NH group have been placed on calculated positions and refined isotropically by using the riding model. The NH proton has been located by difference Fourier maps and refined isotropically. Final indices for 2287 reflections with I > 2σ(Ι): R1 = 0.0588, wR2 = 0.1142, GOF = 1.008. The crystallographic data of 4c have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 912090. Copies of the data can be obtained, free of charge, via the internet (http://www.ccdc.cam.ac.uk/data_request/cif), e-mail (data_request@ccdc.cam.ac.uk), or fax [+44(1223)336033].4-Acetyl-5-(3-chlorophenyl)-2-phenylpyrazolidin-3-one (4d)Yellow powder; mp 118–120 °C; yield: 0.25 g (81%). IR (KBr): 3421, 3063, 2922, 1695, 1593, 1497 cm–1. 1H NMR (500.1 MHz, CDCl3): δ = 2.53 (3 H, s, Me), 3.92 (1 H, d, 3 J = 3.7 Hz, CH), 5.14 (1 H, d, 3 J = 3.7 Hz, CH), 5.27 (1 H, br s, NH), 7.19 (1 H, d, 3 J = 7.5 Hz, CH), 7.23–7.26 (2 H, m, CH), 7.28 (2 H, d, 3 J = 7.3 Hz, CH), 7.40 (2 H, t, 3 J = 7.7 Hz, CH), 7.94 (2 H, t, 3 J = 8.7 Hz, CH) ppm. 13C NMR (125.7 MHz, CDCl3): δ = 30.4 (Me), 57.8 (CH), 66.7 (CH), 119.0 (2 CH), 124.3 (CH), 125.6 (CH), 126.8 (CH), 128.8 (CH), 129.5 (2 CH), 130.9 (CH), 135.3 (C), 138.6 (C), 141.7 (C), 165.3 (C), 201.9 (C) ppm. MS (EI): m/z (%) = 314 (27) [M+], 312 (80), 297 (57), 91 (23), 77 (48). Anal. Calcd for C17H15ClN2O2 (314.77): C, 64.87; H, 4.80; N, 8.90. Found: C, 64.63; H, 4.86; N, 9.00.4-Acetyl-5-(4-chlorophenyl)-2-phenylpyrazolidin-3-one (4e)Yellow powder; mp 105–107 °C; yield: 0.26 g (84%). IR (KBr): 3415, 3051, 2930, 1701, 1580 cm–1. 1H NMR (500.1 MHz, CDCl3): δ = 2.53 (3 H, s, Me), 3.88 (1 H, d, 3 J = 3.4 Hz, CH), 5.13 (1 H, d, 3 J = 3.4 Hz, CH), 5.21 (1 H, br s, NH), 7.18 (1 H, d, 3 J = 7.3 Hz, CH), 7.28 (2 H, d, 3 J = 8.5 Hz, CH), 7.32 (2 H, d, 3 J = 8.5 Hz, CH), 7.39 (2 H, d, 3 J = 8.0 Hz, CH), 7.90 (2 H, d, 3 J = 8.0 Hz, CH) ppm. 13C NMR (125.7 MHz, CDCl3): δ = 29.6 (Me), 57.4 (CH), 66.3 (CH), 118.5 (2 CH), 125.1 (CH), 127.2 (2 CH), 128.8 (2 CH), 129.1 (2 CH), 130.7 (C), 138.2 (C), 138.2 (C), 165.7 (C=O), 201.4 (C=O) ppm. MS (EI): m/z (%) = 314 (27) [M+], 312 (78), 297 (61), 91 (27), 77 (53). Anal. Calcd for C17H15ClN2O2 (314.77): C, 64.87; H, 4.80; N, 8.90. Found: C, 64.57; H, 4.89; N, 9.02.4-Acetyl-5-(3-nitrophenyl)-2-phenylpyrazolidin-3-one (4f)Yellow powder; mp 137–139 °C; yield: 0.31 g (94%). IR (KBr): 3415, 3080, 1704, 1619, 1532 cm–1. 1H NMR (500.1 MHz, CDCl3): δ = 2.55 (3 H, s, Me), 3.92 (1 H, d, 3 J = 3.5 Hz, CH), 5.26 (1 H, br s, NH), 5.30 (1 H, d, 3 J = 3.5 Hz, CH), 7.19 (1 H, t, 3 J = 7.4 Hz, CH), 7.42 (2 H, t, 3 J = 7.3 Hz, CH), 7.53 (1 H, t, 3 J = 7.9 Hz, CH), 7.72 (1 H, d, 3 J = 7.7 Hz, CH), 7.91 (2 H, d, 3 J = 7.6 Hz, CH), 8.15 (1 H, d, 3 J = 8.0 Hz, CH), ppm. 13C NMR (125.7 MHz, CDCl3): δ = 29.7 (Me), 57.0 (CH), 66.4 (CH), 118.4 (2 CH), 121.3 (CH), 123.0 (CH), 125.3 (CH), 129.3 (2 CH), 130.0 (CH), 132.1 (CH), 137.9 (C), 141.6 (C), 148.6 (C), 164.4 (C), 201.0 (C) ppm. MS (EI): m/z (%) = 325 (5) [M+], 323 (75), 308 (55), 308 (61), 91 (51), 77 (55). Anal. Calcd for C17H15N3O4 (325.32): C, 62.76; H, 4.65; N, 12.92. Found: C, 63.07; H, 4.71; N, 13.04.4-Acetyl-5-(4-nitrophenyl)-2-phenylpyrazolidin-3-one (4g)Yellow powder; mp 156–158 °C; yield: 0.30 g (93%). IR (KBr): 3418, 3067, 2923, 1702, 1602, 1520 cm–1. 1H NMR (500.1 MHz, CDCl3): δ = 2.53 (3 H, s, Me), 3.86 (1 H, d, 3 J = 2.8 Hz, CH), 5.14 (1 H, t, 3 J = 2.8 Hz, CH), 5.42 (1 H, br s, NH), 7.19 (1 H, t, 3 J = 7.4 Hz, CH), 7.40 (2 H, t, 3 J = 7.7 Hz, CH), 7.54 (2 H, d, 3 J = 8.5 Hz, CH), 7.90 (2 H, d, 3 J = 8.0 Hz, CH), 8.18 (2 H, d, 3 J = 8.7 Hz, CH) ppm. 13C NMR (125.7 MHz, CDCl3): δ = 29.6 (Me), 57.1 (CH), 66.5 (CH), 118.4 (2 CH), 124.0 (2 CH), 125.3 (CH), 127.0 (2 CH), 129.0 (2 CH), 130.4 (C), 138.0 (C),146.7 (C), 164.4 (C), 200.9 (C) ppm. MS (EI): m/z (%) = 325 (14) [M+], 323 (80), 308 (55), 91 (22), 77 (57). Anal. Calcd for C17H15N3O4 (325.32): C, 62.76; H, 4.65; N, 12.92. Found: C, 62.58; H, 4.72; N, 12.98.4-Acetyl-5-(naphthalen-1-yl)-2-phenylpyrazolidin-3-one (4h)Pale yellow powder; mp 115–117 °C; yield: 0.26 g (80%). IR (KBr): 3424, 3230, 2923, 1668, 1606, 1549, 1497 cm–1. 1H NMR (500.1 MHz, CDCl3): δ = 2.55 (3 H, s, Me), 3.93 (1 H, d, 3 J = 2.9 Hz, CH), 5.43 (1 H, br s, NH), 5.87 (1 H, d, 3 J = 2.9 Hz, CH), 7.20 (1 H, t, 3 J = 7.5 Hz, CH), 7.40–7.45 (3 H, m, CH), 7.52 (2 H, t, 3 J = 7.6 Hz, CH), 7.59 (1 H, d, 3 J = 7.2 Hz, CH), 7.70 (1 H, d, 3 J = 7.3 Hz, CH), 7.80 (1 H, d, 3 J = 7.5 Hz, CH), 7.90 (1 H, d, 3 J = 7.6 Hz, CH), 8.03 (2 H, d, 3 J = 7.2 Hz, CH) ppm. MS (EI): m/z (%) = 330 (6) [M+], 328 (77), 313 (62), 91 (14), 77 (33). Anal. Calcd for C21H18N2O2 (330.38): C, 76.34; H, 5.49; N, 8.48. Found: C, 76.69; H, 5.55; N, 8.57. N-Methyl-N′-[1-(4-methylphenyl)methylidene]-3-oxobutanohydrazide (6a)Pale yellow powder; mp 82–84 °C; yield: 0.18 g (77%). IR (KBr): 3430, 2924, 2857, 1687, 1607 cm–1. 1H NMR (500.1 MHz, CDCl3): δ = 2.26 (3 H, s, Me), 2.37 (3 H, s, Me), 3.39 (3 H, s, CH3N), 3.93 (2 H, s, CH2), 7.19 (2 H, d, 3 J = 8.0 Hz, CH), 7.50 (2 H, d, 3 J = 8.0 Hz, CH), 7.66 (1 H, s, CH) ppm. 13C NMR (125.7 MHz, CDCl3): δ = 21.4 (Me), 27.7 (Me), 29.9 (CH3N), 50.4 (CH2), 125.6 (C), 127.0 (2 CH), 128.5 (2 CH), 131.5 (C), 140.3 (CH), 168.9 (C), 202.0 (C) ppm. MS (EI): m/z (%) = 232 (18) [M+], 148 (55), 91 (28), 84 (80), 77 (10), 51 (55). Anal. Calcd for C13H16N2O2 (232.28): C, 67.22; H, 6.94; N, 12.06. Found: C, 66.89; H, 6.97; N, 12.15. N-Methyl-N′-[1-(4-nitrophenyl)methylidene]-3-oxobutanohydrazide (6b)Pale yellow powder; mp 156–158 °C; yield: 0.25 g (95%). IR (KBr): 3425, 2930, 1687, 1607 cm–1. 1H NMR (500.1 MHz, CDCl3): δ = 2.27 (3 H, s, Me), 3.43 (3 H, s, CH3N), 3.97 (2 H, s, CH2), 7.66 (2 H, d, 3 J = 7.1 Hz, CH), 8.27 (2 H, d, 3 J = 7.1 Hz, CH) ppm. 13C NMR (125.7 MHz, CDCl3): δ = 28.1 (Me), 29.9 (CH3N), 50.4 (CH2), 124.2 (2 CH), 127.6 (2 CH), 140.2 (C), 148.2 (C), 169.0 (C), 201.4 (C) ppm. MS (EI): m/z (%) = 263 (13) [M+], 136 (25), 91 (21), 77 (11). Anal. Calcd for C12H13N3O4 (263.2): C, 54.75; H, 4.98; N, 15.96. Found: C, 55.03; H, 5.06; N, 16.08. N′-[1-(4-Chlorophenyl)methylidene)]-N-(4-methyl-phenyl)-3-oxobutanohydrazide (6c)Yellow solid; mp 94–96 °C; yield: 0.21 g (67%). IR (KBr): 3435, 2920, 2861, 1701, 1607 cm–1. 1H NMR (500.1 MHz, CDCl3): δ = 2.33 (3 H, s, Me), 2.43 (3 H, s, Me), 4.06 (2 H, s, CH2), 7.08 (2 H, d, 3 J = 7.9 Hz, CH), 7.21 (1 H, s, CH), 7.33 (2 H, d, 3 J = 8.1 Hz, CH), 7.36 (2 H, d, 3 J = 7.9 Hz, CH), 7.43 (2 H, d, 3 J = 8.1 Hz, CH) ppm. MS (EI): m/z (%) = 328 (3) [M+], 271 (21), 77 (13). Anal. Calcd for C18H17ClN2O2 (328.80): C, 65.75; H, 5.21; N, 8.52. Found: C, 65.38; H, 5.28; N, 8.61. N′-[1-(3-Nitrophenyl)methylidene)]-N-(4-methyl-phenyl)-3-oxobutanohydrazide (6d)Yellow solid; mp 105–107 °C; yield 0.24 g (71%). IR (KBr): 3425, 2930, 1687, 1607 cm–1. 1H NMR (500.1 MHz, CDCl3): δ = 2.40 (3 H, s, Me), 2.54 (1 H, d, 3 J = 3.5 Hz, CH), 2.95 (2 H, s, CH2), 7.41–45 (2 H, m, CH), 7.16 (1 H, s, CH), 7.65 (1 H, d, 3 J = 7.6 Hz, CH), 7.83 (2 H, d, 3 J = 7.6 Hz, CH), 8.30 (1 H, d, 3 J = 7.6 Hz, CH) ppm. MS (EI): m/z (%) = 339 (4) [M+], 282 (14), 77 (11). Anal. Calcd for C18H17N3O4 (339.35): C, 63.71; H, 5.05; N, 12.38. Found: C, 63.96; H, 5.08; N, 12.46.
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