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DOI:
10.1055/sos-SD-110-00001
Joule, J. A., Science of Synthesis Knowledge Updates, (2010) 2, 51.
A strategy that can be used to bring about the combination of a methylene ketone 187 with an aniline which does not have a halogen ortho to the amine group applies to the special situation where a nitro group on the aromatic ring, e.g. as in 186, allows nucleophilic addition of the ketone enolate.[210,211] Scheme 61 gives some examples, showing the usual products to be 4-nitro-1H-indoles 188 but note that using more substituted ketones gives rise to appreciable quantities of the isomeric 6-nitro-1H-indoles, for example 189 from butan-2-one.[211]
Meeeee 88 Meeee-8M-eeeeeee eeee 8-Meeeeeeeeeeee eee Meeeeee[888]
| M8 | M8 | Meeee (%) | Mee |
|---|---|---|---|
| M | Me | 88 | [888] |
| M | eeeeeeeeeee | 88 | [888] |
| M | 8-eeeeeee | 88 | [888] |
References
| [210] | Meeeeeee, M.; Meeeeee, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
| [211] | Meeeeeee, M.; Meeeeeeeeeeee, M.; Meeeeee, M., Meeeeeeeeee, (8888) 88, 888. |
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