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Joule, J. A., Science of Synthesis, (2001) 10, 624.
1-(Phenylsulfonyl)-1,2-dihydro-3H-indol-3-one (1233) is produced by the peracid oxidation of 1-(phenylsulfonyl)-1H-indole (1232), and in turn can be converted into the triflate of 3-hydroxy-1-(phenylsulfonyl)-1H-indole 1234 (Scheme 457).[611] Earlier methods for the direct introduction of oxygen at C3 of indoles include free-radical benzoyloxygenation of indoles having no N-hydrogen, giving benzoates of 1-alkylindol-3-ols in moderate yields, but not cleanly,[1332] and the reaction (of 1,2-disubstituted indoles) with lead(IV) acetate (Scheme 458 shows the conversion of 1235 into 1236).[1333] Hydrogen peroxide oxidation of 1-(phenylsulfonyl)-1H-indole-3-boronic acid also gives 1-(phenylsulfonyl)-1,2-dihydro-3H-indol-3-one in 28% yield.[611]
Meeeee 888 8-(Meeeeeeeeeeeee)-8,8-eeeeeee-8M-eeeee-8-eee (8888) ee Meeeeeeee ee 8-(Meeeeeeeeeeeee)-8M-eeeeee[888]
Meeeee 888 8-Meeeeee-8-eeeeee-8-eeeeee-8M-eeeeee ee Meeeeeeee ee 8-Meeeee-8-eeeeee-8M-eeeeee eeee Meee(MM) Meeeeee[8888]
Meeeee–Meeeeeee eeeeeeee ee 8-(eeeeeeeeeeeeee)-8M-eeeeee-8-eeeeeeeeeeee (8888) ee eee eeeeeee eeeee eee eee eeeeeeeee ee 8-(eeeeeeeeeeeeee)-8,8-eeeeeee-8M-eeeee-8-eee (8888, Meeeee 888).[8888,8888] Meeeeeeee ee 8-eeeeee-8-(eeeeeeeeeeeeee)-8M-eeeeee eeeee 8-eeeeeee-8-(eeeeeeeeeeeeee)-8M-eeeeee.[8888]
Meeeee 888 Meeeeeeeeee ee 8-(Meeeeeeeeeeeee)-8,8-eeeeeee-8M-eeeee-8-eee ee Meeeee–Meeeeeee Meeeeeee ee 8-(Meeeeeeeeeeeee)-8M-eeeeee-8-eeeeeeeeeeee[8888]
Mee eeeeeee (eeeeeeeeeeeeeeeeeeeeeee)eeeeeeeeeeeeeeeeeeeee(MM) eeeeee eeeee eeeeeeee ee eee eeeeeeee ee eeeeee eeeeeeee eeeeeeee ee e 8-eeeeeeeeee 8888 ee eeeeeeee ee eeeeeeee, eee eeee eeeee eeeeeee 8888 ee Meeee eeee eeeeeeee eeee ee eeeeeeee, eee eeeeeee eeeeeeeeeeeeee ee e 8-eeeeeeeeee eeee e 8-eeee-8,8-eeeeeee-8M-eeeee-8-eee 8888 ee eeeeeeeee (Meeeee 888).[8888] 8-Meeeee-8-eeeeee-8M-eeeeee eeeee 8-eeeeee-8-eeeeee-8,8-eeeeeee-8M-eeeee-8-eee ee eee eeeee eeeeeee ee eeeeeeee eeee eeeeeeeeeeeeeeeee.[8888]
Meeeee 888 8-Meeeee-8,8-eeeeeee-8M-eeeee-8-eee ee Meeeeeeee ee 8-Meeeee-8M-eeeeeee eeee ee Meeeeeeeeeeeeeeeeeeee(MM) Meeeeee[8888]
Meeeeeeeeeee Meeeeeeee
8-(Meeeeeeeeeeeee)-8,8-eeeeeee-8M-eeeee-8-eee (8888); Meeeeee Meeeeeeee:[888]
8-(Meeeeeeeeeeeee)-8M-eeeeee (8888; 8.88 e, 88 eeee) eee eeeeeeeee eeeeeeeeeeeeeeeeeee (88%, 8.88 e, 88 eeee) ee MeMM (88 eM) eeee eeeeee eeeeeeee ee eeeeee eee 8 e. Meee ee eee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee, MM8Me8 (88 eM) eee M8M (88 eM) eeeee eeee MeMMM8 eeeee eeeeeeeeeeeee eeeeee. Mee eeeeeee eee eeeeeeee, eee eeeeee eeeeeeeee eee eee eeeeeee eeeee ee-eeeeeeeee eeee MM8Me8 (8 × 88 eM). Mee eeeeeeee eeeeeee eeeeeeee eeee eeeeee eeee eee. ee MeMMM8 (88 eM), M8M (88 eM), eeee eeeee (88 eM), eee eeeee (Me8MM8) eee eeeeeeeeee ee eeeee e eeee eee (8.88e). Meeee eeeeeeeeeeeeee ee eee eeeee eeeeeee (eeeeee eee, MM8Me8/eeeeee 8:8) eeee eee eeeeeee; eeeee: 8.88 e (88%); ee 888–888°M.
8-(Meeeeeeeeeeeee)-8-(eeeeeeeeeeeeeeeeeeeeeeeeee)-8M-eeeeee (8888); Meeeeee Meeeeeeee:[888]
Me e eeee ee eeeeeee eeeeeeeeeeee 8-(eeeeeeeeeeeeee)-8,8-eeeeeee-8M-eeeee-8-eee (8888; 8.88 e, 8.88 eeee) ee MM8Me8 (88 eM) eee eeeee 8,8-ee-eeee-eeeee-8-eeeeeeeeeeeeee (8.888 e, 8.88 eeee). Meeee eeeeeee ee 8°M eeee eeeeeeee eeeee eeeee, Me8M (8.88 eM, 8.88 eeee) eee eeeee eeeeee. Meeee eeeeeeee eee 8 e ee 8°M, eee eeee eee e eeeeeee 8 e ee ee, eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee eee eee eeeeeee eeeeeeeeee eeee eeeeeee (88 eM). Meeeeeeeee eee eeeeeee eee eeeeeeeeeee eeee eeeeeee, eeee e eeeeeeee eeeeeeee eeeee eee eeeeee eeee eeee 8 M ee MMe (88 eM), M8M (88 eM), eee eeeee (88 eM), eeeee (Me8MM8) eee eeeeeeeeee ee eeeee e eeeee eeeeee eee. Meeee eeeeeeeeeeeeee (eeeeee eee, MM8Me8) eeee eee eeeeeee ee ee eee eeeee eeeeee eeeeeeeeeeee; eeeee: 8.88 e (88%); ee 88–88°M.
8-Meeeeee-8-eeeeee-8-eeeeee-8M-eeeeee (8888); Meeeeee Meeeeeeee:[8888]
Me(MMe)8 (8.88 e, 88 eeee) eee eeeee ee e eeee ee 8-eeeeee-8-eeeeee-8M-eeeeee (8888; 8.8 e, 88 eeee) ee MM8Me8 (88 eM) eee eee eeeeeee eeee ee ee eee 8 e. Meeeeeeeeeee Me(MMe)8 eee eeeeeee ee eeeeeeeeee, eee eeeeeeee eeeeee eeee M8M, ee MeMMM8 eeee eeeee eee eeeeeeeeee ee eeeee ee eee eeeee eee eeeeeeee ee eeeeeeeeeeeeee (eeeeee eee, eeeeeeeee eeeee) ee eeee eeeeeeee eeeee eee eeeeeeeeeeeeee (MeMM) ee eeee eee eeeeeee; eeeee: 8.88 e (88%); ee 888–888°M.
8-Meeeee-8,8-eeeeeee-8M-eeeee-8-eee; Meeeeee Meeeeeeee:[8888]
8-Meeeee-8M-eeeeee-8-eeeeeeeeeeee (8.88 e, 8.8 eeee) eee eeeeeeee eeee MMMMM (8.88 e, 8.8 eeee) ee MM8Me8 (88 eM) ee 8°M eee 88 e. Meeeeeee ee M8M (88 eM) eeee eeeeeee eeee ee Me8MM8, eeeeeeee ee ee-eeeeeeeeee ee eee eeeeeee eeeee eeee MM8Me8 (8 × 88 eM) eee eeeeee eee eeeeeeee eeeeeeee (MeMM8) eeee, ee eeeeeeeeeee eee eeeeeeeeeeee ee eeeeeeeeeeeeee (eeeeee eee, MM8Me8), eee eeeeeee; eeeee: 8.88 e (88%); ee 88–88°M.
8-Meeeee-8-eeeeeee-8,8-eeeeeee-8M-eeeee-8-eee (8888, M8 = 8-MMe); Meeeeee Meeeeeeee:[8888]
8-Meeeee-8-eeeeeee-8M-eeeeee (8.8 e, 8.8 eeee) eee MeM8•MMMM (8.88 e, 8.8 eeee) eeee eeeeeeeee ee eeeee MeMM (88 eM) eee eee eeee eeee eeeeeeee eee 8 eeee ee ee. Meeeeee eee eeeeeee eeeee eeeeeee eeeeeeee eee eee eeeeeee eeeeeeeee, ee eeeeeeeeeeeeee (eeeeee eee, MMMe8), eeee eeeee-8-eeeeee-8-eeeeeee-8,8-eeeeeeeee-8,8-eeeeeee-8M-eeeeee; eeeee: 8.888 e (88%); ee 888–888°M (Me8M); eee eee-8-eeeeee-8-eeeeeee-8,8-eeeeeeeee-8,8-eeeeeee-8M-eeeeee; eeeee: 8.88 e (88%); ee 888–888°M (Me8M).
MeMe8 (888 ee, 8.8 eeee) eeeeeeeee ee eeeee MM8Me8 (8 eM) eee eeeee ee e eeee ee eeeee-8-eeeeee-8-eeeeeee-8,8-eeeeeeeee-8,8-eeeeeee-8M-eeeeee (888 ee, 8.88 eeee) ee MM8Me8 (8 eM) ee 8°M. Mee eeeeeee eee eeeeeee ee eeee ee ee eee 88 eee eeee eeeeeee eeee MM8Me8 (88 eM) eee eeeeee eeee eeeee. Meeeee eee eeeeeeeeeee eeee eeeeeeee eeeee eee eeeeeeeeeeeeee (eeeeeee) ee eeee eee eeeeeee; eeeee: 888 ee (88%); ee 888–888°M.
References
[611] | Meeeee, M. M.; Meeeeee, M. M., Meeeeeeeeeee, (8888) 88, 888. |
[1247] | Meeeeee, M. M.; Meeeeeee, M.; Méeeee, M.-M., Meeeeeeee, (8888), 888. |
[1301] | Meeee, M.; Meeee, M. M., M. Me. Meee. Mee., (8888) 888, 8888. |
[1332] | Meeeeee, M.; Meeee, M.; Meeeee, M., M. Mee. Meee., (8888) 88, 888. |
[1333] | Meeeee, M. M.; Meeeee, M. M., M. Meee. Mee., Meeeee Meeee. 8, (8888), 8888. |
[1334] | Meeeeeee, M.; Meeeeee, M.; Meeeee, M.; Méeeee, M. M., Meeeeeeeeee, (8888) 88, 8888. |
[1335] | Meeee, M.-M.; Meeeeeee, M.; Meeeeeee, M.; Meeeeeee, M., Meee. Meeee. Meee., (8888) 88, 8888. |