Oxidative Access to Quinolinone Derivatives with Simultaneous Rearrangement of Functional Groups

Yoshiharu Amano; Keisuke Inoue; Shigeru Nishiyama

doi:10.1055/s-2007-1000829

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Synlett 2008(1): 134-136
DOI: 10.1055/s-2007-1000829

LETTER

Oxidative Access to Quinolinone Derivatives with Simultaneous Rearrangement of Functional Groups

Yoshiharu Amano, Keisuke Inoue, Shigeru Nishiyama*
Department of Chemistry, Faculty of Science and Technology, Keio University, Hiyoshi 3-14-1, Kohoku-ku, Yokohama 2238522, Japan
Fax: +81(45)5661717; e-Mail: nisiyama@chem.keio.ac.jp;

Further Information

Publication History

Received 27 September 2007
Publication Date:
11 December 2007 (online)

Abstract
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Abstract

Hypervalent iodine-mediated oxidation of aromatic compounds carrying methoxyamide side chains provided the corresponding quinolinones. The reactive point was at the para position to electron-donating groups (such as a MeO group) in the aromatic ring. Introduction of AcO or halogen groups to this position resulted in a cyclization, concomitant with rearrangement of the functional group.

Key words

quinolinone synthesis - oxidations - cyclizations - rearrangements - hypervalent iodine

References and Notes

For examples of synthetic methodology of quinolines, see:
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4

General Procedure for Oxidation with Preoxidized Iodobenzene: A solution of iodobenzene (0.5 mmol, 2 equiv mol) in TFE (25 mL) containing LiClO₄ was electrolyzed (CCE at 0.3 mA/cm², 2.5 F/mol, a glassy carbon beaker as an anode and a platinum wire as a cathode). After electrolysis, the substrate (0.25 mmol) was added to the mixture. After stirring for 30 min, the reaction mixture was diluted with H₂O and extracted with EtOAc. The organic layer was dried (MgSO₄) and evaporated. The residue was chromatographed on preparative TLC to give products.

5

Selected spectroscopic data of new compounds 3-16.Compound 3: ¹H NMR (400 MHz, CDCl₃): δ = 8.81 (br s, 1 H), 6.92 (d, J = 8.8 Hz, 1 H), 6.74-6.77 (m, 2 H), 3.75 (s, 3 H), 3.62 (s, 3 H), 2.84 (t, J = 7.6 Hz, 2 H), 2.27-2.31 (m, 5 H). 4a: ¹H NMR (400 MHz, CDCl₃): δ = 6.64 (d, J = 2.8 Hz, 1 H), 6.49 (d, J = 2.8 Hz, 1 H), 3.78 (s, 3 H), 3.73 (s, 3 H), 2.87 (t, J = 7.2 Hz, 2 H), 2.66 (t, J = 7.2 Hz, 2 H), 2.27 (s, 3 H). Compound 5: ¹H NMR (400 MHz, CDCl₃): δ = 8.85 (br s, 1 H), 7.22 (d, J = 8.8 Hz, 1 H), 6.80 (d, J = 3.0 Hz, 1 H), 6.70 (dd, J = 3.0, 8.8 Hz, 1 H), 3.75 (s, 3 H), 3.69 (s, 3 H), 3.04 (t, J = 7.8 Hz, 2 H), 2.40-2.75 (m, 2 H). HRMS: m/z [M - MeO] calcd for C₁₀H₁₁ ³⁵ClNO₂: 212.0473; found: 212.0454. Compound 6a: ¹H NMR (400 MHz, CDCl₃): δ = 6.84 (d, J = 3.0 Hz, 1 H), 6.64 (d, J = 3.0 Hz, 1 H), 3.86 (s, 3 H), 3.79 (s, 3 H), 2.88 (t, J = 7.0 Hz, 2 H), 2.67 (t, J = 7.0 Hz, 2 H). HRMS: m/z [M] calcd for C₁₁H₁₂ ³⁵ClNO₃: 241.0505; found: 241.0521. Compound 6c: ¹H NMR (400 MHz, CDCl₃): δ = 6.87 (s, 1 H), 6.68 (s, 1 H), 3.90 (s, 3 H), 3.88 (s, 3 H), 2.83 (t, J = 7.6 Hz, 2 H), 2.68 (t, J = 7.6 Hz, 2 H). Compound 7: ¹H NMR (400 MHz, CDCl₃): δ = 8.12 (br s, 1 H), 7.41 (d, J = 8.8 Hz, 1 H), 6.83 (d, J = 2.6 Hz, 1 H), 6.66 (dd, J = 2.6, 8.8 Hz, 1 H), 3.77 (s, 3 H), 3.70 (s, 3 H), 3.06 (t, J = 7.8 Hz, 2 H), 2.39-2.75 (m, 2 H). HRMS: m/z [M] calcd for C₁₁H₁₄ ⁸¹BrNO₃: 289.0136; found: 289.0110. Compound 8a: ¹H NMR (400 MHz, CDCl₃): δ = 7.05 (d, J = 2.6 Hz, 1 H), 6.69 (d, J = 2.6 Hz, 1 H), 3.79 (s, 3 H), 3.78 (s, 3 H), 2.88 (t, J = 7.0 Hz, 2 H), 2.67 (d, J = 7.0 Hz, 2 H). HRMS: m/z [M + H] calcd for C₁₁H₁₃ ⁷⁹BrNO₃: 286.0078; found: 286.0085. Compound 8c: ¹H NMR (400 MHz, CDCl₃): δ = 7.41 (s, 1 H), 6.73 (s, 1 H), 3.91 (s, 3 H), 3.87 (s, 3 H), 2.88 (t, J = 7.0 Hz, 2 H), 2.69 (t, J = 7.0 Hz, 2 H). HRMS: m/z [M + H] calcd for C₁₁H₁₃ ⁷⁹BrNO₃: 286.0079; found: 286.0113. Compound 9: ¹H NMR (400 MHz, CDCl₃): δ = 8.34 (s, 1 H), 7.55 (d, J = 8.0 Hz, 1 H), 6.90 (d, J = 2.4 Hz, 1 H), 6.81 (dd, J = 2.4, 8.0 Hz, 1 H), 3.84 (s, 3 H), 3.72 (s, 3 H), 3.16 (t, J = 7.6 Hz, 2 H), 2.46-2.80 (m, 2 H). HRMS: m/z [M + H - MeO] calcd for C₁₁H₁₂N₂O₂: 204.0897; found: 204.0879. Compound 10b: ¹H NMR (400 MHz, CDCl₃): δ = 7.42 (d, J = 8.4 Hz, 1 H), 6.94 (d, J = 8.4 Hz, 1 H), 4.01 (s, 3 H), 3.98 (s, 3 H), 3.14 (t, J = 7.6 Hz, 2 H), 2.74 (t, J = 7.6 Hz, 2 H). HRMS: m/z [M + H - MeO] calcd for C₁₁H₁₀N₂O₂: 202.0742; found: 202.0769. Compound 11: ¹H NMR (400 MHz, CDCl₃): δ = 8.84 (br s, 1 H), 7.29-7.41 (m, 5 H), 7.17 (t, J = 7.6 Hz, 1 H), 6.77-6.82 (m, 3 H), 5.02 (s, 2 H), 3.63 (s, 3 H), 2.92 (t, J = 7.6 Hz, 2 H), 2.34-2.75 (m, 2 H). Compound 12a: ¹H NMR (400 MHz, CDCl₃): δ = 7.31-7.41 (m, 5 H), 7.11 (d, J = 8.8 Hz, 1 H), 6.85 (dd, J = 2.4, 8.8 Hz, 1 H), 6.79 (d, J = 2.4 Hz, 1 H), 5.02 (s, 2 H), 3.88 (s, 3 H), 2.85 (d, J = 7.4 Hz, 2 H), 2.65 (d, J = 7.4 Hz, 2 H). Compound 13: ¹H NMR (400 MHz, CDCl₃): δ = 8.47 (br s, 1 H), 7.21-7.29 (m, 5 H), 6.70-6.83 (m, 3 H), 4.90 (s, 2 H), 3.50 (s, 3 H), 2.74 (t, J = 7.4 Hz, 2 H), 2.14-2.60 (m, 5 H). Compound 14a: ¹H NMR (400 MHz, CDCl₃): δ = 7.29-7.34 (m, 5 H), 6.64 (d, J = 2.6 Hz, 1 H), 6.51 (d, J = 2.6 Hz, 1 H), 4.94 (s, 2 H), 3.66 (s, 3 H), 2.80 (t, J = 7.0 Hz, 2 H), 2.59 (t, J = 7.0 Hz, 2 H), 2.20 (s, 3 H). Compound 15: ¹H NMR (400 MHz, CDCl₃): δ = 8.74 (br s, 1 H), 7.24 (d, J = 8.1 Hz, 1 H), 6.85-6.93 (m, 2 H), 3.59 (s, 3 H), 2.87 (t, J = 7.6 Hz, 2 H), 2.24-2.70 (m, 8 H). Compound 16: ¹H NMR (400 MHz, CDCl₃): δ = 8.49 (br s, 1 H), 7.31 (d, J = 8.4 Hz, 1 H), 6.99 (d, J = 2.7 Hz, 1 H), 6.89 (dd, J = 2.7, 8.4 Hz, 1 H), 3.64 (s, 3 H), 3.04 (t, J = 7.4 Hz, 2 H), 2.25-2.75 (m, 5 H). HRMS: m/z [M + H] calcd for C₁₂H₁₅ ³⁵ClNO₄: 272.0688; found: 272.0690.

6

This compound was slightly contaminated with 6a.