Nisaburo Ikeda

Oxidation with Fremy's salt—VIII : Peri-effect of a group located at the C5 position of 1-naphthol and related compounds☆

Abstract It has been shown by a series of experiments on 5-alkyl, 5-halo-, and other 5-substituted 1-naphthol derivatives that the product ratio of the ortho - and para -naphthoquinones formed on oxidation with Fremys salt is controlled by the bulkiness of the C 5 -substituent.

Fischer indolization and its related compounds—VII : Development of abnormal fischer indolization of ortho-methoxyphenylhydrazone to provide a synthetic method for useful indole derivatives possessing an active methine group at C6 and novel 3,6′-biindole derivatives☆☆☆

Abstract Fischer indolization of ethyl pyruvate 2-methoxyphenylhydrazone ( 1 ) with p -toluene-sulfonic acid in benzene in the presence of an enolizable dicarbonyl or an indolic compound gave either an indole product having an active methine group at C 6 or a novel type of 3,6′-biindole compound. Structures of the products were established by NMR spectra and chemical evidence.

MECHANISM OF C-C BOND FORMATION DURING FISCHER INDOLIZATION AND PSEUDOCONTACT SHIFT OF ETHYL INDOLE-2-CARBOXYLATE DERIVATIVES

Die Cyclisierung von Brenztraubensaure-phenylhydrazonen nach Fischer zu Indolen wie (I) wird ausfuhrlich untersucht.