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2005
Indole derivatives
R 0140
Indole Synthesis by Controlled Carbolithiation of o-Aminostyrenes. — The new
reaction sequence to afford indoles involves alkyllithium addition to a styrene
12- 121 cascade
double bond and subsequent trapping of the intermediate organolithium with a suitable
electrophile, followed by in situ ring closure and dehydration to generate the indole
ring. The sequence is successfully performed with o-aminostyrenes bearing C and N
substituents, and tert-, sec-, and n-butyllithiums. Indoles unsubstituted at the 2-position
are obtained by addition of DMF (III) as the electrophile (to be continued). —
(KESSLER, A.; COLEMAN, C. M.; CHAROENYING, P.; O'SHEA*, D. F.; J. Org.
Chem. 69 (2004) 23, 7836-pp; Dep. Chem., Univ. Coll., Belfield, Dublin 4, Ire.;
Eng.) — Klein
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