Lewis acid-mediated synthesis of mono- and tris-indole adducts from chiral aziridines was written by Macha, Lingamurthy;Singh, Deepak;Rhee, Hyong-Jin;Ha, Hyun-Joon. And the article was included in Organic & Biomolecular Chemistry in 2020.Synthetic Route of C8H6FN This article mentions the following:
Lewis acid-mediated regio- and stereoselective nucleophilic addition of 2- or 3-substituted indoles to non-activated aziridine-2-carboxaldehydes in dioxane afforded 2-(indol-3-ylhydroxymethyl)aziridines such as I [R = cyclohexyl, Bn, CH(Me)Ph; R1 = H, 5-F, 5-Br, etc.; R2 = 2-CO2Me, CO2Et] whose ring opening with various nucleophiles rendered multi-substituted tryptamine derivatives, e.g., II. The reaction of the same aziridine-2-carboxaldehyde with three moles of indole in dichloromethane yielded tris-indole adducts, e.g., III 尾-(3,3′-bisindolyl)methyl (BIM) tryptamines from sequential steps including nucleophilic addition to aldehyde, Michael type Friedel-Crafts alkylation of the mono-adduct followed by regio- and stereoselective ring-opening of the aziridine ring. In the experiment, the researchers used many compounds, for example, 7-Fluoroindole (cas: 387-44-0Synthetic Route of C8H6FN).
7-Fluoroindole (cas: 387-44-0) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. Indole plays a fundamental role for QS in E. coli, being one of the signal molecules responsible for the transcription of a variety of genes (gabT, and tnaB ASTD). Synthetic Route of C8H6FN
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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