106698-05-9Relevant academic research and scientific papers
A Novel Synthesis of 1-Acylindoxyls
Chien, Chun-Sheng,Hasegawa, Atsushi,Kawasaki, Tomomi,Sakamoto, Masanori
, p. 1493 - 1496 (2007/10/02)
A novel and efficient synthesis of 1-acylindoxyls (3) from 1-acylindoles (1) is described.The procedure involves the demethoxylation with stannic chloride of 1-acyl-3-hydroxy-2-methoxy-indoline (2), which were obtained by the MoO5 oxidation of 1 in methanol.Since the MoO5 oxidation of 2-substituted 1-acylindoles (1f and 1g) gave not the corresponding indolines (2f and 2g), but 2-hydroxyindoxyls (4f and 4g), 2f and 2g were obtained by the methylation of 4f and 4g with diazomethane to give 5f and 5g, followed by the reduction of 5f and 5g with sodium borohydride, respectively.Keywords - indoxyl; indole; indoline; oxidation; demethoxylation; peroxomolybdenum complex; methylation; diazomethane; reduction; sodium borohydride
