By Richard J. Sundberg
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Extra info for The Chemistry of Indoles
Stroh and Hahn have effected the alkylation of 2-methyl-, 2,3-dimethyl-, 2,3,5-trimethyl-, and 2-phenylindole at C-7. The position of substitution has been established by compari son with authentic samples in several cases. It has been suggested that coordination with the aluminum atom may be involved in determining the position of alkylation (243). Aniline derivatives undergo alkylation in the ortho position under similar conditions. T CHo:^Cri2 Al(NHPh) 3 ^^^N^Me Et G68 H. G69 REACTIONS W I T H CARBENES It has been known for some time that application of the Reimer-Tiemann aldehyde synthesis to indoles gives not only indole-3-carboxaldehydes but also 3-chloroquinolines (205).
The reaction has been adapted to quantitative determination of indoles (129). Burr and Gortner (39) have demonstrated qualitatively that the position of the equilibrium between the diindolylmethane J24 and the alkylindene3/f-indole J23 is a function of the acidity of the solution, strongly acidic media favoring J23. Condensation of aromatic aldehydes with indoles in H n CXzx ^ ΠΓΊΓ ΑΗ_ ΓΊΠ H J23 H Me Me x J24 + PhCHO H J25 strongly acidic solution can be used as a preparative route to 3-arylidene3/f-indoles, the synthesis of J28 being a recent example (225).
When indole is condensed with 1,4-diketones, carbazoles are formed from condensation reactions involving both C-2 and C-3 (214). 48 Q I. ELECTROPHILIC SUBSTITUTION Me Me (Me)2CO -H+ N^^Me H H J57 J56 Me I ^CH 2 N^ H H+ J58 Me Me Me Ν ^ ^Μ H MeΓ ^ Ν J57 Me v /Me J54 or J55 <- J60 Me J. CH2CH2COMe + J65 J68 HH J H J69 (34%) 50 □ I. ELECTROPHILIC SUBSTITUTION 0-vH+ CH 2 CH 2 CMe %J Me Me^N H J68 J65 Me, J70 H+ -^ H Me sr xlD H J72 J71 -> J73 OH -J— -CH2CH2CL,il2L,M2U—Π r^ J69 H J. REACTIONS WITH KETONES AND ALDEHYDES □ 51 Me C02Et + MeCOCH 2 C0 2 Et N^^Me H ■£f Me J74 H J76 J75 Me O II J74 + Me MeCOCH 2 COMe INT H x Me J78 J77 Me Mev /OH -CH2COR Q N ^ Me H J79 Me CH2COR N ^ M e H J81 J82 CuCcO Me\^CH2COR g MeMe J] J83 52 Q l.