THE HYDROGENOLYSIS OF 3-HYDROXYMETHYLINDOLE AND OTHER INDOLE DERIVATIVES WITH LITHIUM ALUMINUM HYDRIDE
- 1 September 1953
- journal article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 31 (9), 775-784
- https://doi.org/10.1139/v53-106
Abstract
Indole-3-aldehyde, indole-3-carboxylic acid and its ethyl ester were reduced by excess lithium aluminum hydride to skatole. The expected reduction product, 3-hydroxymethylindole, was obtained by the action of sodium hydroxide on gramine methiodide. It and its alkyl ethers were readily reduced to skatole. 3-Hydroxymethylindole underwent self-condensation to 3,3′-di-indolylmethane in neutral and alkaline media, and with acidic reagents was converted to an oxygen-free polymeric substance. The mechanism of these reactions and of the hydrogenolysis is discussedKeywords
This publication has 20 references indexed in Scilit:
- Ein weiterer Beitrag zur Konstitutionsaufklärung des CorynantheinsHelvetica Chimica Acta, 1953
- The Synthesis of 1,2-Benzo-7,8-(2',3'-indolo)-tetrahydroquinolizine1Journal of the American Chemical Society, 1952
- The Reaction of Gramine with Methyl Iodide. The Preparation and Properties of Gramine MethiodideJournal of the American Chemical Society, 1952
- Reduktion von Ergosteryl‐ und 7‐Dehydro‐cholesteryltosylat mit LithiumaluminiumhydridHelvetica Chimica Acta, 1952
- The structure of uroroseinBiochemical Journal, 1952
- Lithium Aluminum Hydride Reduction of Pyridine Carboxylic Esters: Synthesis of Vitamin B6Journal of the American Chemical Society, 1951
- Thiazole Analogs of PyridoxineJournal of the American Chemical Society, 1950
- Über China‐Alkaloide. 7. Mitteilung. Über die Konstitution von Cinchonamin und ChinaminHelvetica Chimica Acta, 1950
- Intensities of vibration bands. Part II.—Bending vibrations of substituted benzenes and the dipole of the C—H linkTransactions of the Faraday Society, 1950
- Structural Investigations upon a Substituted Dipyrrylmethane. An Unusual Melting Point-Symmetry Relationship1,2Journal of the American Chemical Society, 1942