Studies on Indole Derivatives. XXV. Syntheses of Indoxyl Derivatives.(5). Reaction of 1-Acetyl-3-indolinone with Carbon Disulfide and Reaction of These Products

The reaction of 1-acetyl-3-indolinone with carbon disulfide in the presence of sodium hydride gave anhydro-1-mercapto-3-methyl-9-oxo (9H) thiazolo [3, 4-a] indolium hydroxide. Use of excess carbon disulfide and sodium hydroxide, followed by treatment with dimethyl sulfategave 3, 4-dihydro-1-methylthio-3-(methylthio) thiocarbonylmethyleneimidazo [1, 5-a]-indol-9(9H)-one (XI). Reaction of III with primary amines resulted in the formation of 2-substituted anhydro-1-mercapto-3-methyl-9-oxo (9H)-imidazo [1, 5-a] indolium hydroxides (IXa-e), which are a mesoionic compound having an imidazo [1, 5-a] indolium ring system. Reaction of III with hydrazines gave 10-hydroxy-3-methyl-2H-(1, 2, 4)-triazino [4, 5-a] indole-2-thiones (Xa, b).