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Please login to access the full content or check if you have access via10.13.4.1.1.2.1.2 Method 2: From o-Aminoaryl Halomethyl Ketones; Sugasawa Indoxyl Synthesis
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Joule, J. A., Science of Synthesis, (2001) 10, 621.
The ability to C-acylate anilines regioselectively ortho to the nitrogen (see also Section 10.13.1.1.1.2.1.7) permits the synthesis of o-(chloroacetyl)arylamines 1220 directly from the arylamine. It is a simple matter to bring about the intramolecular displacement of the halide by the amino group and thus provide one of the best ways in which to synthesize 1,2-dihydro-3H-indol-3-ones (indoxyls) 1221 (Scheme 452).[317] Sodium hydride at 0°C effects ring closure of the o-(chloroacetyl)arylamines, and potassium carbonate suffices with N-trifluoroacetyl o-(chloroacetyl)arylamines.
Meeeee 888 Mee Meeeeeee Meeeeee (8,8-Meeeeee-8M-eeeee-8-eee) Meeeeeeee[888]
Meee eeeee ee eeee eee eee eeeeeeeee ee 8-(eeeeeeeeeeeeee)-8,8-eeeeeee-8M-eeeee-8-eee (8888) eeee 8-(eeeeeeeeeee)-M-(eeeeeeeeeeeeee)eeeeeee (8888), eeeeeeee ee eeee eeee ee eeeeeeeeeee ee e eeeeeeeee 8-eeeeeeeeeeeee 8888 (Meeeee 888).[888]
Meeeee 888 Meeeeeeeeee ee 8-(Meeeeeeeeeeeee)-8,8-eeeeeee-8M-eeeee-8-eee eee eee Meeeeeee Meeeeeeee[888]
Meeeeeeeeeee Meeeeeeee
8-Meeeee-8,8-eeeeeee-8M-eeeee-8-eee (8888, M8 = Me; M8 = M); Meeeeee Meeeeeeee:[888]
M-Meeeee-8-(eeeeeeeeeeee)eeeeeee (8.8 eeeee) eeeeeeeee ee eeeeeeeee (8 eM) eee eeeee ee e eeeeeee eeeeeeeeee ee MeM (8.88 eeeee) ee MMM (8 eM) eeee eee eeeeeee. Meeee eeeeeeee eee 8 e, eee eee 8 M ee MMe eeee eeeee eee eeeeeee eeeeeeeee eeee MM8Me8; eeeeeeeeeeee ee eeeeeeeeeeeeee (eeeeee eee, eeeeeee), eeee eeeeeeeeeeeeeeeee (MM8Me8/eeeeee) eeee eee eeeeeee; eeeee: 88%; ee 888–888°M.
8-(Meeeeeeeeeeeee)-8,8-eeeeeee-8M-eeeee-8-eee (8888); Meeeeee Meeeeeeee:[888]
M eeeeeee ee 8-eeeeee-M-(eeeeeeeeeeeeee)eeeeeee (8888; 8.88 e, 88 eeee) eee MeMe8 (8.88 e, 88 eeee) ee MMMe8/MeMMe (8:8, 88 eM) eee eeeeee ee eeeeee eee 88 e. M eeeeee eeeeeeeeeeee eeeeee eee eeeee eee eeee eee eeeeeee eeeeeeee. Meeee eeeeeee ee 8°M eeeee eeeee, Me8M (8.88 eM, 88.8 eeee) eee eeeee eeeeee. Meeee e eeeeeee 8 e ee 8°M, eee eeeeeeee eeee eee eeeeeeee eee, eee eeeeeeeeeee eeeeee eeee eeee MeMMe. Mee eeeeeeee eee eeeeee eeeeeeeeeeee eeee 8 M ee MMe (88 eM), M8M (88 eM), eee eeeee (88 eM), eeee eeeee (Me8MM8) eee eeeeeeeeee ee eeeee e eeeeeee eeeee eee eeeeeeeeeeeeee (Me8M) ee eeee eee eeeeeee; eeeee: 8.88 e (88% eee 8 eeeee); ee 888–888°M.
References
[317] | Meeeeeee, M.; Meeeee, M.; Meeeeeee, M.; Meeeeeee, M., M. Mee. Meee., (8888) 88, 888. |
[611] | Meeeee, M. M.; Meeeeee, M. M., Meeeeeeeeeee, (8888) 88, 888. |