By Richard J. Sundberg
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The acid-catalyzed reaction of 2-methylindole and certain 1,3-dicarbonyl compounds has been examined and the products have been found to be 3-vinylindoles such as J76 and J78 (173). The formation of products such as J76 and J78 may involve a preference for dehydrations of the addition intermediate J79 to J80 rather than to J81, or J81 may be formed and go to J80 faster than it reacts with an indole molecule to give the diindolylmethane J83. The conjugation present in the vinylindole J80 no doubt makes it of lower energy than J81.
268) G31 G33 nitrobenzene , G31 CuBr Ref. (201) G34 G35 Ref. (158) CuBr 2 G36 G37 G38 + 1-isomer (G39) 28 □ i. ELECTROPHILIC SUBSTITUTION Og-D Mgl O' G41 G40 G42 Indolylmagnesium iodide reacts with cyclohexene oxide and is alkylated at the 3-position (90). Alky lat ions of the magnesium derivatives of indole Me I P\ H Me f N G43 SnCU v\ C0 2 Et /CHCHC0 2 Et CCU ^ ^ \ / H G44 (-10%) OH N G45 with propylene oxide (217) and of 2-phenylindole with ethylene oxide (37) have also been reported. In the latter case use of 2 moles of ethylene oxide gave a 48% yield of l,3-bis(2-hydroxyethyl)-2-phenylindole.
A. novel alkylation of indole with ethylene and trianilinoaluminum is reported to give 7-substituted products (244). 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.