Science of Synthesis

Joule, J. A., Science of Synthesis Knowledge Updates, (2010) 2, 67.

In this variant, an N-acyl-o-haloarylamine ‌231‌ (or urethane) is subjected to metal–halogen exchange after deprotonating the N-hydrogen, and then the organolithium species ‌232‌ is reacted with an α-halo ketone ‌233‌ (‌Scheme 84‌).[‌261‌,‌262‌] In some instances the initial product of addition to the carbonyl group can be obtained, but more usually a second step takes place in situ involving the N—C2 bond formation giving ‌234‌; if necessary, a subsequent simple dehydration is all that is required to obtain the indole. For photocyclizations of ortho-substituted anilines with ketones see Houben–Weyl, Vol. E 19a, pp 1023–1026, 1225–1227.

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8,8,8,8-Meeeeeeeee-8M-eeeeeeeee (‌88‌); Meeeeee Meeeeeeee:[‌888‌]

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References