Chemistry of Aminochromes. Part XV. The Reaction of Epinochrome with Thiols

Abstract

Epinochrome (5) has been shown to react with thioglycollic acid to give mainly 5,6-dihydroxy-I-methylindoline and a 4-thiosubstituted 5,6-dihydroxy-1-methylindoline. The acetyl derivatives of these compounds (i.r. 7b and 15), along with that of the corresponding 4-thiosubstituted 5.6-dihydroxyindole (i.e. l l ) , were isolated after acetylation of the reaction mixture. The latter compound is probably a secondary product of the reaction, having arisen from the 4-thiosubstituted 5,6-dihydroxy-1-methylindoline which is formed initially.On a montre que I'epinochrome (5) reagit avec I'acide thioglycolique pour conduire principalement au dihydroxy-5,6 methyl-1 indoline et au dihydroxy-5,6 methyl-l indoline thiosubstitue en position 4. Les derives acetyles de ces composes (c'est-a-dire 7b et 15) de m&me que ceux qui correspondent au dihydroxy-5,6 indole thiosubstitue en position 4 (par exemple 11) ont etC isoles a p r b acetylation du melange reactionnel. Le dernier compose est probablement un produit secondaire de la reaction provenant du dihydroxy-5.6 methyl-1 indoline thiosubstitue en position 4 qui s'est initialement forme.