Novel Synthesis of 2-Amino-1,4-benzoquinone-4-phenylimides from Anilines via Dess-Martin Periodinane Oxidation

Abstract

A synthetic investigation on oxidation of anilines to 2-amino-1,4-benzoquinone-4-phenylimides via Dess-Martin periodinane (DMP) was carried out. This facile protocol offered the advantage of short reaction times, mild reaction conditions, high yields and compatibility with a wide range of functional groups.

iminoquinone - periodinane - oxidation

References and Notes

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17

CCDC 643540 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.

18

General Procedure: H₂O (54 mg, 3.0 mmol) and aniline (1.5 mmol) were added to a solution of DMP (1.3 g, 2.64 mmol) in CH₂Cl₂ (8 mL). The mixture was stirred at r.t. until complete consumption of the aniline (observed by TLC). The solution was washed with H₂O (5 × 8 mL) and the organic phase was dried over anhyd Na₂SO₄. After filtration, the solvent was removed and the residue was purified by silica gel column chromatography to afford the final compound.

19

2-Amino-3-chloro-1,4-benzoquinone-4-(2-chloro)phenyl-imide (6b): bright red-orange solid; mp 128-130 °C. IR (KBr): 3475, 3370, 1653, 1623, 1598, 1562, 1392, 1338, 838, 766, 754 cm^-1. ¹H NMR (400 MHz, CDCl₃): δ = 7.43 (d, J = 5.0 Hz, 1 H), 7.25 (t, J = 4.8 Hz, 1 H), 7.10 (t, J = 4.8 Hz, 1 H), 6.76-6.82 (m, 2 H), 6.44 (d, J = 6.3 Hz, 1 H), 5.10 (s, 2 H). ¹³C NMR (100 MHz, CDCl₃): δ = 180.95, 153.72, 146.74, 140.81, 129.89, 129.49, 129.04, 126.93, 126.02, 124.77, 121.48, 111.99. MS (FAB): m/z = 266.8 [M + H⁺]. Anal. Calcd for C₁₂H₈Cl₂N₂O: C, 53.96; H, 3.02; N, 10.49. Found: C, 53.92; H, 2.98; N, 10.52.

20 Liu L. Zhang Y. Wang Y. J. Org. Chem.  2005,  70:  6122