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DOI: 10.1055/s-2007-984516
Novel Synthesis of 2-Amino-1,4-benzoquinone-4-phenylimides from Anilines via Dess-Martin Periodinane Oxidation
Publication History
Publication Date:
25 June 2007 (online)
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.
Key words
iminoquinone - periodinane - oxidation
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References and Notes
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.
18General 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.
192-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.