Efficient Synthesis of Functionalized Pyrido[2,3-c]coumarin Derivatives by a One-Pot Three-Component Reaction

Zhiwei Chen; Lele Hu; Fei Peng

doi:10.1055/s-0035-1561610

Synlett, Inhaltsverzeichnis

Synlett 2016; 27(12): 1888-1892
DOI: 10.1055/s-0035-1561610

letter

Efficient Synthesis of Functionalized Pyrido[2,3-c]coumarin Derivatives by a One-Pot Three-Component Reaction

Zhiwei Chen*

^aNational Engineering Research Center for Process Development of Active Pharmaceutical Ingredients, Collaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals, Zhejiang University of Technology, Hangzhou 310014, P. R. of China

^bKey Laboratory for Green Pharmaceutical Technologies and Related Equipment of Ministry of Education, College of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou 310014, P. R. of China eMail: e-mail_chenzhiwei@zjut.edu.cn

,

Lele Hu

^aNational Engineering Research Center for Process Development of Active Pharmaceutical Ingredients, Collaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals, Zhejiang University of Technology, Hangzhou 310014, P. R. of China

^bKey Laboratory for Green Pharmaceutical Technologies and Related Equipment of Ministry of Education, College of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou 310014, P. R. of China eMail: e-mail_chenzhiwei@zjut.edu.cn

,

Fei Peng

^aNational Engineering Research Center for Process Development of Active Pharmaceutical Ingredients, Collaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals, Zhejiang University of Technology, Hangzhou 310014, P. R. of China

^bKey Laboratory for Green Pharmaceutical Technologies and Related Equipment of Ministry of Education, College of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou 310014, P. R. of China eMail: e-mail_chenzhiwei@zjut.edu.cn

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Abstract

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Abstract

A methanesulfonic acid promoted three-component reaction has been developed for the synthesis of functionalized pyrido[2,3-c]coumarin derivatives from ketones, aromatic aldehydes, and 3-aminocoumarin. In this simple and efficient protocol, products were obtained in moderate to good yields (28 examples). The reaction proceeds by an asynchronous [4+2] cycloaddition (inverse-electron-demand Diels–Alder reaction).

Key words

multicomponent reactions - pyridocoumarins - ketones - aldehydes - cycloaddition reactions

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Referenzen

References and Notes

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20 Pyrido[2,3-c]coumarins 4; General Procedure A dry 25 mL flask was charged with 3-aminocoumarin (1a; 1 mmol), aromatic aldehyde 2 (1 mmol), ketone 3 (1 mmol), MsOH (1 mmol), and MeCN (5 mL). The mixture was stirred at the reflux temperature for 2.5−8 h until the reaction was complete (TLC) and then cooled to r.t. The crystalline solids were collected and washed with a little cold MeCN to give the pure product. 3-(3-Chlorophenyl)-1-phenyl-5H-chromeno[3,4-b]pyridin-5-one (4f) Pale-yellow powder; yield: 329 mg (86%); mp 241–243 °C; ¹H NMR (400 MHz, CDCl₃): δ = 8.16 (s, 1 H), 8.09–8.06 (m, 1 H), 7.90 (s, 1 H), 7.57–7.55 (m, 3 H), 7.45–7.38 (m, 4 H), 7.36–7.33 (m, 2 H), 7.04 (d, J = 8.0 Hz, 1 H), 6.89–6.85 (m, 1 H); ¹³C NMR (100 MHz, CDCl₃): δ = 158.9, 155.9, 151.0, 149.3, 139.6, 139.4, 138.9, 135.2, 130.8, 130.3, 129.8, 129.4, 128.9, 128.3, 127.9, 127.7, 127.5, 125.6, 123.9, 117.9, 117.2. HRMS-ESI: m/z [M + H]⁺ calcd for C₂₄H₁₅ClNO₂: 384.0786; found: 384.0794. 3-(1-Naphthyl)-1-phenyl-5H-chromeno[3,4-b]pyridin-5-one (4l) Pale-yellow powder; yield: 331 mg (83%); mp 237–239 °C. ¹H NMR (400 MHz, CDCl₃): δ = 8.24–8.23 (m, 1 H), 7.94–7.91 (m, 2 H), 7.84 (s, 1 H), 7.78–7.77 (m, 1 H), 7.53–7.46 (m, 8 H), 7.39 (d, J = 8.0 Hz, 2 H). 7.11 (d, J = 8.0 Hz, 1 H) 6.92 – 6.88 (m, 1 H), ¹³C NMR (100 MHz, CDCl₃): δ = 159.4, 158.6, 150.8 , 148.2, 139.2, 139.1, 136.1, 133.7, 131.9, 130.8, 130.3, 129.7, 129.3, 128.9, 128.3, 128.2, 128.0, 127.6, 126.8, 125.9, 125.0, 124.9, 123.5, 117.6, 116.9. HRMS-ESI: m/z [M + H]⁺ calcd for C₂₈H₁₈NO₂: 400.1332; found: 400.1327. 3-Phenyl-1-(4-tolyl)-5H-chromeno[3,4-b]pyridin-5-one (4m) Pale-yellow powder; yield: 283 mg (78%); mp 208–210 °C. ¹H NMR (400 MHz,CDCl₃): δ = 8.18–8.15 (m, 2 H), 7.90 (s, 1 H), 7.49–7.41 (m, 3 H), 7.35–7.29 (m, 6 H), 7.11 (d, J = 8.0 Hz, 1 H) 6.90–6.86 (m, 1 H), 2.49 (s, 3 H). ¹³C NMR (100 MHz, CDCl₃): δ = 158.7, 157.1, 150.7, 148.8, 139.0, 138.9, 136.9, 136.6, 130.0, 129.9, 129.9, 128.6, 128.1, 127.9, 127.5, 127.4, 127.1, 123.4, 117.5, 117.1, 21.4. HRMS-ESI: m/z [M + H]⁺ calcd for C₂₅H₁₈NO₂: 364.1332; found: 364.1316. 1-(4-Fluorophenyl)-3-phenyl-5H-chromeno[3,4-b]pyridin-5-one (4p) White powder; yield: 315 mg (86%); mp 278–280 °C. ¹H NMR (400 MHz, DMSO-d ₆): δ = 8.31–8.29 (m, 2 H), 8.22 (s, 1 H), 7.63–7.59 (m, 2 H), 7.57–7.51 (m, 3 H), 7.46–7.40 (m, 4 H), 7.02–6.94 (m, 2 H). ¹³C NMR (100 MHz, CDCl₃): δ = 164.2, 161.8, 158.6, 157.4, 150.8, 147.6, 139.2, 136.9, 135.6, 130.4, 130.1, 130.0, 128.8, 128.0, 127.4, 127.3, 127.2, 123.6, 117.8, 116.9, 116.7, 116.5. HRMS-ESI: m/z [M + H]⁺ calcd for C₂₄H₁₅FNO₂: 368.1081; found: 368.1065. 8-Phenyl-9,10,11,12-tetrahydro-6H-chromeno[3,4-c]isoquinolin-6-one (4v) Pale-yellow powder; yield: 277 mg (85%); mp 217–219 °C. ¹H NMR (400 MHz, CDCl₃): δ = 8.25 (d, J = 8.4 Hz, 1 H), 7.52–7.32 (m, 8 H), 3.36 (s, 2 H), 2.85 (s, 2 H), 1.88 (s, 4 H). ¹³C NMR (100 MHz, CDCl₃): δ = 160.6, 159.1, 150.7, 144.9, 139.3, 137.0, 135.7, 129.8, 129.6, 128.8, 128.1, 128.0, 127.8, 123.7, 118.0, 117.8, 31.7, 28.9, 22.5, 21.6. HRMS-ESI: m/z [M + H]⁺ calcd for C₂₂H₁₈NO₂: 328.1332; found: 328.1323. 2-Methyl-1,3-diphenyl-5H-chromeno[3,4-b]pyridin-5-one (4x) Pale-yellow powder; yield: 268 mg (74%); mp 228–230 °C. ¹H NMR (400 MHz, DMSO-d ₆): δ = 7.68–7.50 (m, 8 H), 7.40–7.35 (m, 4 H), 6.86–6.83 (m, 1 H), 6.63–6.61 (m, 1 H), 2.09 (s, 3 H). ¹³C NMR (100 MHz, CDCl₃): δ = 160.8, 158.9, 150.9, 147.8, 139.3, 138.6, 136.2, 129.9, 129.2, 128.6, 128.5, 128.1, 127.3, 123.5, 117.6, 117.3, 19.3. HRMS-ESI: m/z [M + H]⁺ calcd for C₂₅H₁₈NO₂: 364.1332; found: 364.1315.

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