Facile Synthesis of 2-Aryl-3H-indol-3-ones via Singlet Oxygenation of 2-Arylindoles

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• All new compounds gave consistent elemental and spectral data. Compound 2g; red needles, IR(KBr): 1725 (C=O), 1581, 872, 765 cm−1. MS(El), m/z; 287 (M+2,51.7), 285 (M+,51.2), 259(M+2-CO, 98.3), 257(M-CO. 100). Anal. calcd. for C14H8BrNO:C58.77, H2.82, N4.90, Found:C59.01, H2.78, N4.92.Compound2j:dark red needles, IR(KBr):1721 (C=O), 1597, 1504, 1166cm−1 1HNMR(CDCl3/TMS):1.43 (t,j=6.8Hz, 3H, CH3); 4.11(q,j = 6.8 Hz, 2H, CH2); 6.98, 8.39 (4H, AA′BB′, HC2′, HC2′, HC3′, HC5′), 7.17–7.60 (4H, m, indole ArH) ppm. MS (El) m z: 251 (M+, 48.1)223 (M-CO,100). Anal. calcd. for C16H13NO2 : C 76.47, H 5.21.N 5.58, Found: C 76.50, H 5.33, N5.67. Compound 2k: deep-red microscopic needles. IR(KBr):1721 (C=O),1513,1347 (N=O) cm−1, MS(El)m/z: 252 (M+, 36.6), 224(M-CO,100)Anal.calcd for C14H8N2O3 : C 66.67, H 3.20, N I 1.11, Found: C 66.67, H 3.31, N 10.92
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