Catalyst-Free Synthesis of N-(1,7-Dioxotetrahydropyrazolo[1,2-a]pyrazol-2-yl)benzamide Derivatives by 1,3-Dipolar Cycloaddition and Rearrangement

Wenjing Liu; Yu Xu; Xingxia Sun; Dapeng Lu; Lijuan Guo

doi:10.1055/s-0033-1341056

Synlett, Inhaltsverzeichnis

Synlett 2014; 25(08): 1093-1096
DOI: 10.1055/s-0033-1341056

letter

Catalyst-Free Synthesis of N-(1,7-Dioxotetrahydropyrazolo[1,2-a]pyrazol-2-yl)benzamide Derivatives by 1,3-Dipolar Cycloaddition and Rearrangement

Wenjing Liu

Department of Chemistry and Anhui Key Lab for Biomass Clean Energy, University of Science and Technology of China, Hefei 230026, P. R. of China Fax: +86(551)63606689 eMail: xyu@ustc.edu.cn

,

Yu Xu*

Department of Chemistry and Anhui Key Lab for Biomass Clean Energy, University of Science and Technology of China, Hefei 230026, P. R. of China Fax: +86(551)63606689 eMail: xyu@ustc.edu.cn

,

Xingxia Sun

Department of Chemistry and Anhui Key Lab for Biomass Clean Energy, University of Science and Technology of China, Hefei 230026, P. R. of China Fax: +86(551)63606689 eMail: xyu@ustc.edu.cn

,

Dapeng Lu

Department of Chemistry and Anhui Key Lab for Biomass Clean Energy, University of Science and Technology of China, Hefei 230026, P. R. of China Fax: +86(551)63606689 eMail: xyu@ustc.edu.cn

,

Lijuan Guo

Department of Chemistry and Anhui Key Lab for Biomass Clean Energy, University of Science and Technology of China, Hefei 230026, P. R. of China Fax: +86(551)63606689 eMail: xyu@ustc.edu.cn

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Abstract

Alle Artikel dieser Rubrik

Abstract

N-(1,7-Dioxotetrahydropyrazolo[1,2-a]pyrazol-2-yl)-benzamide derivatives, a novel class of compounds, were synthesized by 1,3-dipolar cycloaddition of azomethine imines with azlactones and subsequent rearrangement. The reaction can be completed rapidly under mild conditions without a catalyst.

Key words

cycloadditions - azomethine imines - azlactones - heterocycles - bicyclic compounds

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Referenzen

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10 N-(1,7-Dioxotetrahydro-1H,5H-pyrazolo[1,2-a]pyrazol-2-yl)benzamides 3a–p; General Procedure Azomethine imine 1 (1.2 equiv, 0.24 mmol), azlactone 2 (0.2 mmol), and CH₂Cl₂ (0.5 mL) were added to a small tube containing a magnetic stirrer, and the mixture were stirred at r.t. for 2–6 h. The crude product was purified by column chromatography [silica gel, EtOAc–PE (1:1)]. N-(3,5-Dioxo-1,2-diphenyltetrahydro-1H,5H-pyrazolo[1,2-a]pyrazol-2-yl)benzamide (3a) White solid; yield: 74.8 mg (91%); mp 191–192 °C; IR (KBr): 3418, 3059, 2929, 2850, 1785, 1676, 1575, 1298, 918, 711 cm^–1; ¹H NMR (400 MHz, CDCl₃): δ = 7.48 (dd, J = 15.3, 7.2 Hz, 5 H), 7.41–7.34 (m, 8 H), 7.24–7.19 (m, 2 H), 6.71 (s, 1 H), 4.77 (s, 1 H), 3.41 (s, 1 H), 3.00–2.81 (m, 3 H); ¹³C NMR (101 MHz, CDCl₃): δ = 165.73, 165.00, 161.93, 135.68, 133.48, 131.83, 131.57, 131.03, 129.47, 128.90, 128.76, 128.71, 128.52, 127.38, 126.86, 126.57, 71.04, 50.17, 35.99; HRMS (ESI): m/z [M + Na]⁺ calcd for C₂₅H₂₁NaN₃O₃: 434.1475; found: 434.1468. N-[1-(4-Methoxyphenyl)-3,5-dioxo-2-phenyltetrahydro-1H,5H-pyrazolo[1,2-a]pyrazol-2-yl]benzamide (3b) White solid; yield: 61.5 mg (70%); mp 159–160 °C; IR (KBr): 3413, 3061, 2932, 1783, 1713, 1597, 1503, 1267, 1173, 1045, 916, 835, 716 cm^–1; ¹H NMR (400 MHz, CDCl₃): δ = 7.54 (d, J = 8.4 Hz, 2 H), 7.45 (t, J = 6.9 Hz, 3 H), 7.38–7.33 (m, 5 H), 7.13 (d, J = 8.7 Hz, 2 H), 6.87 (d, J = 8.8 Hz, 2 H), 6.75 (s, 1 H), 4.68 (s, 1 H), 3.78 (s, 3 H), 3.39 (s, 1 H), 2.99–2.84 (m, 3 H); ¹³C NMR (101 MHz, CDCl₃): δ = 190.77, 165.57, 165.10, 160.22, 135.65, 133.49, 131.91, 131.82, 128.68, 128.59, 128.52, 126.90, 126.56, 122.56, 114.28, 114.24, 70.86, 55.52, 55.02, 35.69; HRMS (ESI): m/z [M + Na]⁺ calcd for C₂₆H₂₃NaN₃O₄: 464.1581; found: 464.1573. N-[1-(4-Fluorophenyl)-3,5-dioxo-2-phenyltetrahydro-1H,5H-pyrazolo[1,2-a]pyrazol-2-yl]benzamide (3d) White solid; yield: 72.6 mg (85%); mp 195–196 °C; IR (KBr): 3414, 3074, 2922, 2851, 1796, 1714, 1644, 1515, 1292, 1222, 1034, 918, 706 cm^–1; ¹H NMR (400 MHz, CDCl₃): δ = 7.48 (dd, J = 18.5, 7.5 Hz, 5 H), 7.44–7.33 (m, 6 H), 7.25 (d, J = 3.1 Hz, 1 H), 7.05 (t, J = 8.5 Hz, 2 H), 6.67 (s, 1 H), 4.82 (s, 1 H), 3.35 (s, 1 H), 3.01–2.88 (m, 3 H); ¹³C NMR (101 MHz, CDCl₃): δ = 166.67, 165.88, 164.86, 164.39, 136.09, 133.29, 132.03, 129.33, 128.98, 128.93, 128.64, 128.53, 127.84, 127.25, 126.86, 126.41, 71.10, 35.71, 29.67; HRMS (ESI): m/z [M + Na]⁺ calcd for C₂₅H₂₀FN₃NaO₃: 452.1381; found: 452.1377. N-[1-(2-Furyl)-3,5-dioxo-2-phenyltetrahydro-1H,5H-pyrazolo[1,2-a]pyrazol-2-yl]benzamide (3l) White solid; yield: 55.2 mg (69%); mp 166–168 °C; IR (KBr): 3424, 2932, 1783, 1713, 1666, 1502, 1314, 904, 730 cm^–1; ¹H NMR (400 MHz, CDCl₃): δ = 7.83 (d, J = 7.1 Hz, 2 H), 7.48–7.31 (m, 10 H), 6.52 (dd, J = 3.2, 0.5 Hz, 1 H), 6.29 (dd, J = 3.3, 1.9 Hz, 1 H), 5.90 (s, 1 H), 3.39–3.34 (m, 1 H), 2.94 (ddd, J = 16.1, 10.9, 9.0 Hz, 1 H), 2.80–2.65 (m, 2 H); ¹³C NMR (101 MHz, CDCl₃): δ = 166.05, 165.50, 163.88, 147.86, 143.87, 135.51, 133.24, 131.71, 128.93, 128.74, 128.39, 126.79, 126.56, 113.92, 110.33, 69.23, 46.41, 35.05; HRMS (ESI): m/z [M + Na]⁺ calcd for C₂₃H₁₉NaN₃O₄: 424.1268; found: 424.1261. N-(1-Cyclohexyl-3,5-dioxo-2-phenyltetrahydro-1H,5H-pyrazolo[1,2-a]pyrazol-2-yl)benzamide (3m) White solid; yield: 35.5 mg (91%); mp 141–143 °C; IR (KBr): 3424, 2920, 1713, 1561, 1444, 1279, 1045, 815, 730 cm^–1; ¹H NMR (400 MHz, CDCl₃): δ = 7.80 (d, J = 7.1 Hz, 2 H), 7.65 (d, J = 7.3 Hz, 2 H), 7.55 (t, J = 8.0 Hz, 1 H), 7.44 (d, J = 12.3 Hz, 4 H), 7.37 (t, J = 6.7 Hz, 1 H), 6.70 (s, 1 H), 3.79 (t, J = 8.1 Hz, 1 H), 3.49 (d, J = 7.5 Hz, 1 H), 3.09 (dd, J = 14.8, 6.9 Hz, 1 H), 2.99–2.91 (m, 1 H), 2.71 (dd, J = 16.4, 6.3 Hz, 1 H), 1.99 (d, J = 11.9 Hz, 1 H), 1.79 (d, J = 16.9 Hz, 2 H), 1.66–1.54 (m, 3 H), 1.20–1.06 (m, 5 H); ¹³C NMR (101 MHz, CDCl₃): δ = 166.70, 165.12, 162.50, 138.27, 132.95, 132.24, 129.03, 128.88, 128.80, 127.11, 126.39, 76.06, 69.93, 56.20, 38.88, 35.96, 31.89, 29.89, 25.56; HRMS (ESI): m/z [M + Na]⁺ calcd for C₂₅H₂₇NaN₃O₃: 440.1945; found: 440.1950.

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