Chapter VIII Hydroxyindoles, Indole Alcohols, and Indolethiols (pages 1–355): Thomas F. Spande
Chapter IX Indole Aldehydes and Ketones (pages 357–527): William A. Remers
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Additional resources for Chemistry of Heterocyclic Compounds: Indoles, Part Three, Volume 25
With EAC and methoxy- (201) or methyl-substituted (202)p-benzoquinone, the 6-substituted 5-hydroxyindoles, 204 and 205, were obtained in 24 and 45% yield. Hydroxy-p-benzoquinone (203)was reported to give the 5,6-dihydroxyindole derivative 206, although the yield was not stated. When 2-hydroxy-5,6-dimethyl-p-benzoquinone (210) was employed, ethyl 2,4,7-trimethyl-5,6-dihydroxyindole-3carboxylate was formed in 48% yield. A one-step saponification and decarboxylation of these materials was developed using boiling dilute 6-methyl alkali under nitrogen and gave the 6-methoxy (m), (m), Chapter VIII 48 H u)1; R=OCH, 202; R=CH, 204, R=OCH, 205; R=CH, 206; R = O H 203; R=OH 207, R = O C H , 208.
EIOH. HOAc I . + I I H H 63; R = H 66; R=CH, 62; R = H 65; R=CH, CH,O sdKm46 I H R 64 R=H 67: R = C H , R 64, 67 Chapter VIIl 28 Baxter and Swan have reported'"' that hydrogenation of l-benzyloxyS-methoxy-2,P-dinitrostyrenewith a palladium catalyst in ethyl acetateethanol-acetic acid gives a mixture of S-methoxy-6-hydroxyindole( 6 % ) and S-methoxy-6-benzyloxyindole( 13%). S-dimethoxy2,P-dinitrostyrene with lithium aluminum hydride in THF afforded 5,6dimethoxyindole in 20% yield along with the major product, 6,7dimethoxycinnoline (68).
The generally modest Chapter VIII 32 yields of the reaction are usually more than offset by the ready availability of the starting materials and the ease of carrying out the reaction. In a few instances, zinc chloride has been employed as an auxiliary catalyst, though there seems no clear-cut justification for this practice. For example, Julia and Lenzi obtained1Is equivalent yields with and without zinc chloride. 1. Nonaromatic a-Haloketones Janetzky and co-workers prepared’ l 6 1,3-dimethyl-S-rnethoxyindole (103)using N-methyl-p-anisidine (W), bromoacetone, and the anisidine hydrochloride (Scheme 9).