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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 26, 1996 - Issue 1
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Original Articles

Synthesis of Bulky 2,2-Diaryl-1,2-dihydro-3H-indol-3-ones via Singlet Oxygenation of 2-Arylindoles

Ling Ke-Qing Department of Chemistry, Huaibei Teacher's College, Supported by Coal Industry Huaibei, Anhui, 235000, China
Pages 149-152 | Received 28 Apr 1995, Published online: 21 Aug 2006

References and Notes

  • Mérour , J. Y. , Coadou , J. Y. and Tatibouët , F. 1982 . Synthesis , : 1053
  • Buzas , A. , Herisson , C. and Lavielle , G. 1977 . Synthesis , : 129
  • Kilminster , K. N. and Sonsburg , M. 1972 . J. Chem. Soc. Perkin Trans. 1 , : 2264
  • Mérour , J. Y. , Chichereau , L. and Finet , J. P. 1992 . Tetrahedron Lett. , 33 : 3867
  • All new compounds gave consistent elemental and spectral data. Compound 2d: yellow plates. IR (KBr): 3368, 3274 (NH), 1689 (C=0), 1613 ()6, 747 cm−1. MS(El) m/z: 5.00; (M+). Anal. calcd. for C36H24N2O: C, 86.37; H, 4.83; N, 5.60. Found: C, 86.42; H, 5.00; N, 5.51. Compound 2g: yellow prisms. IR (KBr): 3225 (NH), 1671 (C=O), 1612 ())6, 741, 700 cm−1. 1HNMR (DMSO-d 6 /TMS): 2.87 (3H, s, CH3), 6.35–8.00 (18H, m, ArH), 8.34 (1H, s, NH) ppm. MS (EI) m/z: 414 (M+). Anal. calcd. for C29 H22N2O: C, 84.03; H, 5.35; N, 6.76. Found: C, 83.91; H, 5.34; N, 6.77. Compound 2j: yellow plates. IR (KBr): 3415 (NH), 1680 (C=O), 1612 ())6, 805, 749, 706 cm−1. 1HNMR (CDCl3): 2.81 (3H, s, CH3), 2.83 (3H, s, CH3), 3.45 (1H, s, NH), 6.50, 7.03 ) 6.69–7.65 (9H, m, Ph and indole ArH) ppm. MS (EI) m/z: (4H, 328 M+). Anal. calcd. for C22H20N2O: C, 80.46; H, 6.14; N, 8.53. Found: C, 80.62; H, 6.17; N, 8.59.
  • Colonna , M. , Greci , L. and Marchetti , L. 1975 . Gazz. Chim. Ital. , 105 : 985
  • Colonna , M. , Greci , L. , Marchetti , L. , Andreetti , G. D. , Bocelli , G. and Sgarabotto , P. 1976 . J. Chem. Soc. Perkin Trans. 2 , : 309
  • Ling , K.-Q. , Liu , Z.-B. and Hu , H.-W. 1994 . Chinese J. Org. Chem. (in Chinese) , 14 : 593
  • Denney , R. W. and Nickon , A. 1973 . Org. Reac. , 20 : 133
  • Saito , I. , Morii , T. , Matsugo , S. and Matsuura , T. 1982 . J. Chem. Soc. Chem. Commun. , : 977
  • Kawasaki , T. , Nonaka , Y. , Kobayashi , M. and Sakamoto , M. 1991 . J. Chem. Soc. Perkin Trans. 1 , : 2445
  • Braudeau , E. , David , S. and Fischer , J.-C. 1974 . Tetrahedron , 30 : 1445
  • Chien , C.-S. , Takanami , T. , Kawasaki , T. and Sakamoto , M. 1985 . Chem. Pharm Bull. , 33 : 1843
  • Berti , C. , Colonna , M. , Greci , L. and Marchetti , L. 1981 . J. Chem. Soc. Chem. Commun. , : 694
  • Colonna , M. , Greci , L. and Marchetti , L. 1974 . Ann. Chim. (Italy) , 64 : 7
  • Richman , R. J. and Hassner , A. 1968 . J. Org. Chem. , 33 : 2548 and references cited therein.

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