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

Issa Yavari; Mohammad J. Bayat; Stavroula Skoulika

doi:10.1055/s-0033-1339642

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Synlett 2013; 24(19): 2591-2595
DOI: 10.1055/s-0033-1339642

letter

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

Issa Yavari*

^aDepartment of Chemistry, Tarbiat Modares University, PO Box 14115-175, Tehran, Iran Fax: +98(21)82883455 Email: yavarisa@modares.ac.ir

,

Mohammad J. Bayat

^aDepartment of Chemistry, Tarbiat Modares University, PO Box 14115-175, Tehran, Iran Fax: +98(21)82883455 Email: yavarisa@modares.ac.ir

,

Stavroula Skoulika

^bLaboratory 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)

Abstract
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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.
31 Burnett AM. N, Johnson CK Oak Ridge National Laboratory Report ORNL-6895, Oak Ridge National Laboratory: Oak Ridge, 1996
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