Indoles. XXII. New synthesis of the indole nucleus. Application to psilocine was written by Julia, Marc;Pascal, Yves R.. And the article was included in Chimica Therapeutica in 1970.Formula: C8H9NO This article mentions the following:
Psilocine (I, R = H, R1 = NMe2) was prepared by Vilsmeier-Haack condensation of pyrrole with H2NOC-CH2CH2CO2Me. Me 4-(2-pyrrolyl)-4-oxobutyrate was reduced (Huang-Minlon) to give 4-(2-pyrrolyl)butyric acid, whose mixed anhydride (from ClCO2Et) was cyclized with SnCl4 or ZnCl2 to 4,5,6,7-tetrahydro-4-indolone, which was aromatized with Pd-C in mesitylene. 4-Hydroxyindole was acetylated, treated with oxalyl chloride and HNMe2, and reduced with LiAlH4 to psilocine. I (R = CH2CH:CH2, iso-Pr, CH2CH2CO2H, R1 = NMe2; R = CH2CH2CONEt2, R1 = OH, Br, or NMe2) were similarly prepared In the experiment, the researchers used many compounds, for example, 6,7-Dihydro-1H-indol-4(5H)-one (cas: 13754-86-4Formula: C8H9NO).
6,7-Dihydro-1H-indol-4(5H)-one (cas: 13754-86-4) belongs to indole derivatives. In addition to tryptophan, indigo, and indoleacetic acid, numerous compounds obtainable from plant or animal sources contain the indole molecular structure. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.Formula: C8H9NO
Referemce:
Indole alkaloid derivatives as building blocks of natural products from聽Bacillus thuringiensis聽and聽Bacillus velezensis聽and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles