THE HYDROGENOLYSIS OF 3-HYDROXYMETHYLINDOLE AND OTHER INDOLE DERIVATIVES WITH LITHIUM ALUMINUM HYDRIDE

作者: Edward Leete , Léo Marion

DOI: 10.1139/V53-106

关键词:

摘要: 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 the action of sodium hydroxide on gramine methiodide. It alkyl ethers readily 3-Hydroxymethylindole underwent self-condensation 3,3′-di-indolylmethane in neutral alkaline media, with acidic reagents converted an oxygen-free polymeric substance. mechanism these reactions hydrogenolysis is discussed

参考文章(19)
H. Schmid, P. Karrer, Über die Umsetzungsprodukte von Toluolsulfonsäureestern mit Lithiumaluminiumhydrid Helvetica Chimica Acta. ,vol. 32, pp. 1371- 1378 ,(1949) , 10.1002/HLCA.19490320504
A. R. H. Cole, H. W. Thompson, Intensities of vibration bands. Part II.—Bending vibrations of substituted benzenes and the dipole of the C—H link Transactions of The Faraday Society. ,vol. 46, pp. 103- 109 ,(1950) , 10.1039/TF9504600103
R. Goutarel, M.-M. Janot, V. Prelog, W. I. Taylor, Über China‐Alkaloide. 7. Mitteilung. Über die Konstitution von Cinchonamin und Chinamin Helvetica Chimica Acta. ,vol. 33, pp. 150- 164 ,(1950) , 10.1002/HLCA.19500330124
N. L. PADDOCK, Role of the solvent in reduction with lithium aluminium hydride. Nature. ,vol. 167, pp. 1070- 1071 ,(1951) , 10.1038/1671070A0
P. Karrer, H. Asmis, Reduktion von Ergosteryl‐ und 7‐Dehydro‐cholesteryltosylat mit Lithiumaluminiumhydrid Helvetica Chimica Acta. ,vol. 35, pp. 1926- 1931 ,(1952) , 10.1002/HLCA.19520350619
H. C. Longuet-Higgins, C. A. Coulson, A theoretical investigation of the distribution of electrons in some heterocyclic molecules containing nitrogen Transactions of The Faraday Society. ,vol. 43, pp. 87- 94 ,(1947) , 10.1039/TF9474300087
P. Karrer, St. Mainoni, Ein weiterer Beitrag zur Konstitutionsaufklärung des Corynantheins Helvetica Chimica Acta. ,vol. 36, pp. 127- 130 ,(1953) , 10.1002/HLCA.19530360118
L. H. Conover, D. S. Tarbell, Thiazole Analogs of Pyridoxine Journal of the American Chemical Society. ,vol. 72, pp. 5221- 5225 ,(1950) , 10.1021/JA01167A121
Reuben G. Jones, Edmund C. Kornfeld, Lithium Aluminum Hydride Reduction of Pyridine Carboxylic Esters: Synthesis of Vitamin B6 Journal of the American Chemical Society. ,vol. 73, pp. 107- 109 ,(1951) , 10.1021/JA01145A040
H. R. Snyder, Ernest L. Eliel, Carbon Alkylations with 1-Methylgramine and its Methiodide Journal of the American Chemical Society. ,vol. 71, pp. 663- 669 ,(1949) , 10.1021/JA01170A079