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Please login to access the full content or check if you have access via10.13.1.1.1.3.1.1.3 Variation 3: From Nb-Aryl Benzophenone Hydrazones and Ketones
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Joule, J. A., Science of Synthesis Knowledge Updates, (2010) 2, 35.
Nb-Aryl benzophenone hydrazones 115 can be obtained via the palladium-catalyzed coupling of aryl bromides with benzophenone hydrazone using palladium(II) acetate with Xantphos. The Fischer synthesis is achieved by a one-pot hydrolysis of the benzophenone Nb-arylhydrazone in the presence of a ketone, indole formation then following.[173] Scheme 42 shows a selection of examples of one-pot formation of indoles 116 from Nb-aryl benzophenone hydrazones 115.
Meeeee 88 Meeeeeeee ee Me-Meee Meeeeeeeeeee Meeeeeeeee eeee Meeeeeeeeee eee Meeeeeeeeeee Meeeeeeee eee Meeee Meeeeeee eeee Meeeeee Me Meee Meeeeee[888,888]
M8 | M8 | M8 | M8 | M8 | Meeee (%) ee 888 | Meeee (%) ee 888 | Mee |
---|---|---|---|---|---|---|---|
M | Me | M | (MM8)8 | 88 | 88 | [888] | |
Me | M | Me | M | MM8Me | 88 | 88 | [888] |
MMe | M | M | Me | Me | 88 | 88 | [888] |
M | MM8 | M | (MM8)8Me | Me | 88 | <8 | [888] |
MMe | MMe | M | Me | Me | 88 | 88 | [888] |
M | M | M | (MM8)8Me | Me | 88e | 88 | [888,888] |
e Meeee Me(MMe)8, 8-(eeeeeeeeeeeeeeeeeeeee)-8′-eeeeeeeeeeeeee (MeMeee), MeMM, 888°M, 8-eeeeeeeeeee-8-ee.
Meeeeeeeeeee Meeeeeeee
8-Meeeee-8,8,8,8-eeeeeeeeee-8M-eeeeeeeee [888, M8 = M8 = M; M8 = Me; M8,M8 = (MM8)8]; Meeeeee Meeeeeeee:[888]
M eeeee-eeeee Meeeeee eeeee eee eeeeeeeee, eeeeeeeeee eeee eeeee, eee eeeeeee eeee Me(MMe)8 (8.8 ee, 8.88 eeee), Meeeeeee (8.8 ee, 8.888 eeee), eee eeeeeee (8 eM). Mee eeeee eee eeee eeeeee eeee e eeeeee, eee eee eeeeeee eee eeeeeee ee ee eeeee eeeee eee eeeeeeeeeeeee 8 eee. Mee eeeeee eee eeeeeee, eee eeeeeeeeeeee eeeeeeeee (8.88 e, 88.8 eeee), 8-eeeeeeeeeeeeeeeeee (8.88 e, 88.8 eeee), eee e-MeMMe (8.88 e, 88 eeee) eeee eeeee ee eee eeeee, eeeeeeee ee ee eeeeeeeeee eeeeeee ee eeeeeee (8 eM). Mee Meeeeee eeeee eee eeeeeeee, eeeeeeeee, eee eeeeeeeeee eeee eeeee, eee eee eeeeeeeeee–eeeeeeee eeeee eee eeeeeeee eeeee eeee. Mee eeee eee eeee eeeeee ee 88°M eeeee eee eeeeeeeeeeee eeeeeeeee eee eeee eeeeee eeee eeeeeeee, ee eeeeeeeeee ee MM eeeeeeee. Mee eeeeeee eee eeee eeeeee ee ee, eee eeeeee eee eeeeeee, eee eee eeeeeee eee eeeeeee eeee Me8M (88 eM). Mee eeeeeeeee eeeeeeeeeeeee eeeeeee eee eeee eeeeeeee eeeeeee e eee ee eeeeee eee, eee eee eeeeee eee eee eeeeee eeee ee eeeeeeeeee eeeeeee ee Me8M (88–88 eM). Mee eeeeeeee eee eeeeeeeeeeee ee eeeeee eee eeeee eeeeeee. Meeeeeeeeeeeeeeee eeee eee eMeMM (888 eM) eeeeeeee eeeeee eeeeeeee ee M-(8-eeeeeeeeeeee) eeeeeeeeeeee eeeeeeeee; eeeee: 8 e (88%); ee 888–888°M.
Mee Me-(8-eeeeeeeeeeee) eeeeeeeeeeee eeeeeeeee (888, M8 = M8 = M; M8 = Me; 888 ee, 8.8 eeee), eeeeeeeeeeeee (888 μM, 8.8 eeee), eee MeMM•M8M (8.8 eeeee) eeee eeeeeeeee ee MeMM (8 eM), eee eee eeee eee eeeeee ee eeeeee eeeee eee eeeeeeee eeeeeeee eee eeeeeeee, ee eeeeeeeeee ee MM eeeeeeee. Mee eeeeeee eee eeeeee ee ee, eeeeeee eeee Me8M (8 eM), eee eeeeeeeeeee eeee e eee. MeMMM8 eeee. Mee eeeeeee eeeee eee eeeeeeeee eeee Me8M (8 × 88 eM), eee eee eeeeeeee eeeeeee eeeeeeee eeee eeeee (M8MM8), eeeeeeee, eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Meeeeeeeeeee ee eee eeeee eeeeeee ee eeeee eeeeeeeeeeeeee (MeMMe/eeeeeee 8:8) eeee eee eeeeee 888 ee e eeeee eeeee; eeeee: 888 ee (88%); ee 888–888°M.
References
[173] | Meeee, M.; Meee, M. M.; Meeeeeee, M. M., M. Me. Meee. Mee., (8888) 888, 88888. |